Acetic Anhydride → HCID 54314519, compound

HRID 1420671Notes

Reaction equation

HRID 1420671 reaction equation
[C@@H:1]1([N:10]2[CH2:15][CH2:14][C:13]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([C:16]#[N:17])[CH2:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(OC(=O)C)(=[O:27])C.[OH-].[Na+]>C(O)=O>[C@@H:1]1([N:10]2[CH2:11][CH2:12][C:13]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([C:16]([NH2:17])=[O:27])[CH2:14][CH2:15]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 53792914HCID 53792914, compound

Product 1

HCID 54314519HCID 54314519, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

(S)-1-Indan-1-yl-4-phenylamino-piperidine-4-carbonitrile (27 mmol) was added dropwise at room temperature to a mixture of acetic anhydride and formic acid (40 ml each). The mixture was stirred for 16 h at room temperature. Sodium hydroxide solution was added (pH=7) and the mixture extracted with ethyl acetate. Organic phases were pooled, dried with sodium sulfate and concentrated. Chromatography on silica gel (ethyl acetate) yielded the formulated amine which was dissolved in t-butanol (60 ml). Ammonia (28%, 10 ml), water (10 ml) and hydrogen peroxide solution (33% in water, 5 ml) were added. The mixture was stirred for 2.5 h at room temperature (RT, about 22° C.), quenched with cold water (50 ml) and extracted with methylene chloride. Organic phases were pooled, dried with sodium sulfate and concentrated. Chromatography on silica gel (methylene chloride/methanol, 98:2) yielded the desired product as a solid. 1.0 g (11%) of (S)-1-indan-1-yl-4-phenylamino-piperidine-4-carboxylic acid amide, m.p. 194-195° C. and MS: m/e=336.2 (M+H+).

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1a319687dae94e90911397c82b84a3c8
Source dataset
uspto-grants-2000_06
Patent number
US06071925

Reaction notes

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