Thionyl Chloride → HCID 9983374, compound

HRID 2108107Notes

Reaction equation

HRID 2108107 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:17][CH3:18])=[CH:5][C:6]2[O:12][CH2:11][CH2:10][C:9]([C:13]([OH:15])=O)=[CH:8][C:7]=2[CH:16]=1.S(Cl)(Cl)=O.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:35]=[C:36]([O:40][CH3:41])[C:37]=1[O:38][CH3:39])[CH2:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>C1(C)C=CC=CC=1.C(Cl)Cl.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[C:4]([O:17][CH3:18])=[CH:5][C:6]2[O:12][CH2:11][CH2:10][C:9]([C:13]([N:32]3[CH2:31][CH2:30][N:29]([CH2:28][C:27]4[CH:35]=[C:36]([O:40][CH3:41])[C:37]([O:38][CH3:39])=[C:25]([O:24][CH3:23])[CH:26]=4)[CH2:34][CH2:33]3)=[O:15])=[CH:8][C:7]=2[CH:16]=1

Participants

7

Reactant 3

HCID 24386Thionyl ChlorideHCID 1040951-[(3,4,5-Trimethoxyphenyl)methyl]piperazineHCID 10037723HCID 10037723, compound

Product 1

HCID 9983374HCID 9983374, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 7,8-dimethoxy-2,3-dihydro-1-benzoxepin-4-carboxylic acid (0.5 g) dissolved in toluene (10 ml) is added thionyl chloride (1.5 ml), followed by stirring for one hour at 100° C. The reaction mixture is concentrated under reduced pressure to give a crude acid chloride, which is dissolved in methylene chloride (8 ml). The solution is added dropwise, while stirring under ice-cooling, to a solution of 1-(3,4,5-trimethoxybenzyl)piperazine (0.78 g) in a mixture of methylene chloride (20 ml) and triethylamine (1.6 ml), followed by stirring for 3 hours. The reaction mixture is poured into ice-water, followed by extraction with methylene chloride. The organic layer is washed with water, dried, and concentrated under reduced pressure. The residue is purified by means of a silica gel column chromatography (eluent: hexane-acetone-ethanol=10:8:1) to afford 1-(7,8-dimethoxy-2,3-dihydro-1-benzoxepin-4-carbonyl)-4-(3,4,5-trimethoxybenzyl)piperazine as a colorless oily product (0.9 g). This product is converted into its hydrochloride, followed by recrystallization from ethanol-ether to give colorless needles, m.p. 208°-210° C.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customto give a crude acid chloride, which
  3. additionThe solution is added dropwise
  4. stirringwhile stirring under ice-
  5. stirringby stirring for 3 hours
  6. extractionfollowed by extraction with methylene chloride
  7. washThe organic layer is washed with water
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is purified by means of a silica gel column chromatography (eluent: hexane-acetone-ethanol=10:8:1)

Sources & evidence

ORD record
ord-2c994b123e0c41a098cb65749d49ca0b
Source dataset
uspto-grants-1990_06
Patent number
US04937246

Reaction notes

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