Acetyl chloride → 1-[7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-methyl-N-(2-{4-acetylamino-3,5-dichloro-phenyl}-ethyl)-amino]-propane

HRID 1154644Notes

Reaction equation

HRID 1154644 reaction equation
[CH3:1][O:2][C:3]1[C:30]([O:31][CH3:32])=[CH:29][C:6]2[CH2:7][C:8](=[O:28])[N:9]([CH2:12][CH2:13][CH2:14][N:15]([CH3:27])[CH2:16][CH2:17][C:18]3[CH:23]=[C:22]([Cl:24])[C:21]([NH2:25])=[C:20]([Cl:26])[CH:19]=3)[CH2:10][CH2:11][C:5]=2[CH:4]=1.C(N(CC)CC)C.[C:40](Cl)(=[O:42])[CH3:41]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:30]([O:31][CH3:32])=[CH:29][C:6]2[CH2:7][C:8](=[O:28])[N:9]([CH2:12][CH2:13][CH2:14][N:15]([CH3:27])[CH2:16][CH2:17][C:18]3[CH:23]=[C:22]([Cl:24])[C:21]([NH:25][C:40](=[O:42])[CH3:41])=[C:20]([Cl:26])[CH:19]=3)[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 133166781-[7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-methyl-N-(2-{4-amino-3,5-dichloro-phenyl}-ethyl)-amino]-propane

Product 1

HCID 204338371-[7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-methyl-N-(2-{4-acetylamino-3,5-dichloro-phenyl}-ethyl)-amino]-propane

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 3 gm (0.0063 mol) of 1-[7,8-dimethoxy-1,3,4,5,-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-methyl-N-(2-{4amino-3,5-dichloro-phenyl}ethyl)-amino]-propane in 50 ml of chloroform and 0.7 gm (0.007 mol) of triethylamine was mixed at the boiling point in portions with altogether about 0.8 ml of acetyl chloride. After boiling it for several hours, the reaction mixture was cooled to room temperature and washed with water. The aqueous phase was made strongly alkaline with 2N sodium hydroxide and extracted with methylene chloride. The separated organic phase was dried over sodium sulfate and evaporated. The crude product thus obtained was purified by chromatography on silica gel (particle size: 0.063 to 0.2 mm, eluant: methylene chloride/methanol=8:1).

Workup

  1. customfor several hours
  2. washwashed with water
  3. extractionextracted with methylene chloride
  4. dry with materialThe separated organic phase was dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-9187d780c62e4130a550bbb55068b081
Source dataset
uspto-grants-1984_12
Patent number
US04490369

Reaction notes

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