Acetyl chloride → HCID 19607876, compound

HRID 1603147Notes

Reaction equation

HRID 1603147 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-12f793c8b8f74f1aac2befb19769480b
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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