Triethylamine → HCID 10007850, compound

HRID 358786Notes

Reaction equation

HRID 358786 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([O:22][CH3:23])[C:19]=1[O:20][CH3:21])[CH2:6][N:7]1[CH2:12][CH2:11][NH:10][CH:9]([CH2:13][CH2:14][CH2:15][OH:16])[CH2:8]1.C(N(CC)CC)C.[CH3:31][O:32][C:33]1[C:34]([O:47][CH3:48])=[CH:35][C:36]2[CH2:42][CH2:41][CH2:40][C:39]([C:43](Cl)=[O:44])=[CH:38][C:37]=2[CH:46]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:31][O:32][C:33]1[C:34]([O:47][CH3:48])=[CH:35][C:36]2[CH2:42][CH2:41][CH2:40][C:39]([C:43]([N:10]3[CH2:11][CH2:12][N:7]([CH2:6][C:5]4[CH:17]=[C:18]([O:22][CH3:23])[C:19]([O:20][CH3:21])=[C:3]([O:2][CH3:1])[CH:4]=4)[CH2:8][CH:9]3[CH2:13][CH2:14][CH2:15][OH:16])=[O:44])=[CH:38][C:37]=2[CH:46]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 10264946HCID 10264946, compoundHCID 10426420HCID 10426420, compound

Product 1

HCID 10007850HCID 10007850, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4-(3,4,5-trimethoxybenzyl)-2-piperazine propanol (1.0 g) obtained in Reference Example 32, triethylamine (1.5 g) and methylene chloride (20 ml) is added dropwise at 0 ° C, while stirring, a solution of 2,3-dimethoxy-6,7-dihydro-5H-benzocycloheptene-8-carbonyl chloride (713 mg) in methylene chloride (5 ml). The mixture is stirred for 2 hours and there is added an aqueous solution of sodium hydrogencarbonate, followed by shaking. The organic layer is separated, washed with water, dried and concentrated under reduced pressure. The concentrate is purified by means of a silica gel column chromatography (eluent:ethyl acetate-hexane methanol=5:4:1), followed by recrystallization from ethyl acetate to give 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl) -4-(3,4,5-trimethoxybenzyl)-2-piperazine propanol as colorless prisms (1.05 g), m.p. 144-145° C.

Workup

  1. additionis added dropwise at 0 ° C
  2. stirringThe mixture is stirred for 2 hours
  3. stirringby shaking
  4. customThe organic layer is separated
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe concentrate is purified by means of a silica gel column chromatography (eluent:ethyl acetate-hexane methanol=5:4:1)
  9. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-968f2df965e04d128c96c18193228bc8
Source dataset
uspto-grants-1991_03
Patent number
US04997836

Reaction notes

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