Dimethyl Sulfoxide → HCID 10460299, compound

HRID 358784Notes

Reaction equation

HRID 358784 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][C:13]1[C:14]([O:47][CH3:48])=[CH:15][C:16]2[CH2:22][CH2:21][CH2:20][C:19]([C:23]([N:25]3[CH2:30][CH2:29][N:28]([CH2:31][C:32]4[CH:37]=[C:36]([O:38][CH3:39])[C:35]([O:40][CH3:41])=[C:34]([O:42][CH3:43])[CH:33]=4)[CH2:27][CH:26]3[CH2:44]O)=[O:24])=[CH:18][C:17]=2[CH:46]=1.[CH2:49]([N:51](CC)[CH2:52]C)C>C(Cl)Cl>[CH3:11][O:12][C:13]1[C:14]([O:47][CH3:48])=[CH:15][C:16]2[CH2:22][CH2:21][CH2:20][C:19]([C:23]([N:25]3[CH2:30][CH2:29][N:28]([CH2:31][C:32]4[CH:33]=[C:34]([O:42][CH3:43])[C:35]([O:40][CH3:41])=[C:36]([O:38][CH3:39])[CH:37]=4)[CH2:27][CH:26]3[CH2:44][N:51]([CH3:52])[CH3:49])=[O:24])=[CH:18][C:17]=2[CH:46]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 10436901HCID 10436901, compound

Product 1

HCID 10460299HCID 10460299, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of oxalyl chloride (175 mg) in methylene chloride (1 ml) is added dropwise at -78° C. a solution of dimethyl sulfoxide (215 mg) in methylene chloride (1 ml), and the mixture is stirred for 10 minutes. To the reaction mixture is added a solution of 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl) -4-(3,4,5-trimethoxybenzyl)piperazine-2-methanol (500 mg) in methylene chloride (2 ml), and the mixture is stirred for 10 minutes. To the reaction mixture is added triethylamine (650 mg), then the reaction temperature is raised up to room temperature. To the reaction mixture is then added water, followed by extraction with methylene chloride. The organic layer is washed with water, dried and concentrated under reduced pressure. The concentrate is dissolved in methanol (5 ml). To the mixture are added dimethylamine hydrochloride (200 mg) and sodium cyanoborohydride (130 mg). The reaction mixture is stirred for 48 hours at room temperature and then poured into a 1N NaOH solution, followed by extraction with methylene chloride. The organic layer is washed with water, dried and concentrated under reduced pressure. The concentrate is purified by means of a silica gel column chromatography (eluent:methanol ethyl acetate=15:85) to give 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl) -2-dimethylaminomethyl-4-(3,4,5-trimethoxybenzyl) piperazine (200 mg). This product is converted to its hydrochloride, followed by recrystallization from ethanol to give colorless prisms, m.p. 167-169° C.

Workup

  1. stirringthe mixture is stirred for 10 minutes
  2. extractionadded water, followed by extraction with methylene chloride
  3. washThe organic layer is washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe concentrate is dissolved in methanol (5 ml)
  7. additionTo the mixture are added dimethylamine hydrochloride (200 mg) and sodium cyanoborohydride (130 mg)
  8. stirringThe reaction mixture is stirred for 48 hours at room temperature
  9. additionpoured into a 1N NaOH solution
  10. extractionfollowed by extraction with methylene chloride
  11. washThe organic layer is washed with water
  12. customdried
  13. concentrationconcentrated under reduced pressure
  14. customThe concentrate is purified by means of a silica gel column chromatography (eluent:methanol ethyl acetate=15:85)

Sources & evidence

ORD record
ord-6fa62e9be38b40409eb1ef350e83a094
Source dataset
uspto-grants-1991_03
Patent number
US04997836

Reaction notes

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