Acetyl chloride → HCID 19607876, compound

HRID 745104Notes

Reaction equation

HRID 745104 reaction equation
[CH3:1][N:2]([CH:13]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]([C:24](=[O:41])[C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:40])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[CH3:39])=[CH:27][CH:26]=2)[CH2:16][CH2:15][CH2:14]1)[CH2:3][CH2:4][CH2:5][O:6][CH:7]1[CH2:12]CCC[O:8]1.C(Cl)(=O)C>C(O)(=O)C>[CH3:1][N:2]([CH:13]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]([C:24](=[O:41])[C:25]2[CH:26]=[CH:27][C:28]([NH:31][C:32](=[O:40])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[CH3:39])=[CH:29][CH:30]=2)[CH2:16][CH2:15][CH2:14]1)[CH2:3][CH2:4][CH2:5][O:6][C:7](=[O:8])[CH3:12]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 19607827HCID 19607827, compound

Product 1

HCID 19607876HCID 19607876, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 5-{N-methyl-N-[3-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propyl]amino}-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.4 g) is added a mixture of acetyl chloride (0.5 ml) and acetic acid (5 ml) at room temperature, and the mixture is stirred overnight. The reaction solution is concentrated and the resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=30:1), and further purified again by silica gel column chromatography (eluent; n-hexane:ethyl acetate=1:2) to give 5-[N-methyl-N-(3-acetyloxypropyl)amino]-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.06 g) as colorless amorphous.

Workup

  1. concentrationThe reaction solution is concentrated
  2. customthe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=30:1)
  3. customfurther purified again by silica gel column chromatography (eluent; n-hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-590827ee5f634936a3dc89003ee2f1d1
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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