Acetic Anhydride → HCID 21538621, compound

HRID 1076892Notes

Reaction equation

HRID 1076892 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:26])[CH2:9][CH2:10][CH2:11][N:12]2[CH2:16][CH2:15][C:14]3([C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]([OH:25])[CH2:17]3)[CH2:13]2)=[CH:4][CH:3]=1.[C:27](OC(=O)C)(=[O:29])[CH3:28].[OH-].[Na+]>N1C=CC=CC=1>[C:27]([O:25][CH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14]2([CH2:15][CH2:16][N:12]([CH2:11][CH2:10][CH2:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[O:26])[CH2:13]2)[CH2:17]1)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 54334119HCID 54334119, compound

Product 1

HCID 21538621HCID 21538621, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

7.5 g of (1RS,3RS)-p-fluoro-4-(3-hydroxy-spiro[indane-1,3'-pyrrolidin]-1'-yl)butyrophenone are stirred at room temperature for 20 hours together with 15 cc of pyridine and 15 cc of acetic anhydride. The reaction mixture is then poured on ice, is made alkaline with 2 N caustic soda solution and is extracted thrice with 100 cc amounts of ether. The crude title compound obtained as oily residue after concentrating the ether phase by evaporation, is converted into the hydrogen fumarate form, which is recrystallized from ethanol/ether. M.P. of the hydrogen fumarate form of the title compound: 168°-170°.

Workup

  1. additionThe reaction mixture is then poured on ice
  2. extractionis extracted thrice with 100 cc amounts of ether

Sources & evidence

ORD record
ord-1ffd1afab34149a7914e75be8a956bd9
Source dataset
uspto-grants-1976_05
Patent number
US03958003

Reaction notes

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