Acetic Anhydride → HCID 18620767, compound

HRID 1861707Notes

Reaction equation

HRID 1861707 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][C:12]([C:14]2[CH:22]=[CH:21][C:20]3[NH:19][CH2:18][CH:17]4[CH2:23][CH2:24][CH2:25][C:15]=2[C:16]=34)=[O:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:26](OC(=O)C)(=[O:28])[CH3:27]>C(OCC)(=O)C>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([CH2:10][CH2:11][C:12]([C:14]2[CH:22]=[CH:21][C:20]3[N:19]([C:26](=[O:28])[CH3:27])[CH2:18][CH:17]4[CH2:23][CH2:24][CH2:25][C:15]=2[C:16]=34)=[O:13])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 186210833-(1-Acetyl-4-piperidinyl)-1-(1,2,2a,3,4,5-hexahydrobenz[cd]indol-6-yl)-1-propanone

Product 1

HCID 18620767HCID 18620767, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixed solution of 3-(1-acetyl-4-piperidinyl)-1-(1,2,2a,3,4,5-hexahydrobenz[cd]indol-6-yl)-1-propanone (free base, 0.15 g, 0.44 mmol) and acetic anhydride (0.066 ml, 0.69 mmol) in ethyl acetate (20 ml) was heated at 70-75° C. with stirring for 1 hour. The solvent was then distilled off and the residue was purified by silica gel column chromatography (eluent: ethyl acetate-methanol=20:1) to provide the title compound (0.155 g) as colorless crystals melting at 130-132° C.

Workup

  1. distillationThe solvent was then distilled off
  2. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate-methanol=20:1)

Sources & evidence

ORD record
ord-3eb6e936d7004355b85875423c5a225d
Source dataset
uspto-grants-2003_03
Patent number
US06534496B1

Reaction notes

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