Acetyl chloride → HCID 19607876, compound

HRID 1291668Notes

Reaction equation

HRID 1291668 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-c62b89a9a7ce49269613d83ce8c0507a
Source dataset
uspto-grants-1998_05
Patent number
US05753677

Reaction notes

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