Acetic Anhydride → HCID 10291701, compound

HRID 1861706Notes

Reaction equation

HRID 1861706 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][C:9]([C:11]2[CH:12]=[C:13]3[C:18]4=[C:19]([CH2:21][CH2:22][N:17]4[C:16](=[O:23])[CH2:15][CH2:14]3)[CH:20]=2)=[O:10])[CH2:3][CH2:2]1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>C(OCC)(=O)C>[C:24]([N:1]1[CH2:2][CH2:3][CH:4]([CH2:7][CH2:8][C:9]([C:11]2[CH:12]=[C:13]3[C:18]4=[C:19]([CH2:21][CH2:22][N:17]4[C:16](=[O:23])[CH2:15][CH2:14]3)[CH:20]=2)=[O:10])[CH2:5][CH2:6]1)(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 99665448-[3-(4-piperidinyl)propanoyl]1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one

Product 1

HCID 10291701HCID 10291701, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixed solution of 8-[3-(4-piperidinyl)-1-oxopropyl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one (free base, 0.30 g, 0.96 mmol) and acetic anhydride (0.11 ml, 1.16 mmol) in ethyl acetate (25 ml) was heated at 55-60° 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=10:1) to provide the title compound (0.185 g) as colorless powders melting at 160-161° C.

Workup

  1. distillationThe solvent was then distilled off
  2. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate-methanol=10:1)

Sources & evidence

ORD record
ord-1611e96ed75e4b3282c21f179b63468c
Source dataset
uspto-grants-2003_03
Patent number
US06534496B1

Reaction notes

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