Acetic Anhydride → HCID 66737933, compound

HRID 1641297Notes

Reaction equation

HRID 1641297 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27](OC(=O)C)(=[O:29])[CH3:28].[NH4+].[OH-]>O>[C:27]([N:19]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)[C:11]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10]1)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 66738128HCID 66738128, compound

Product 1

HCID 66737933HCID 66737933, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 0.2 g (0.56 mmol) ethyl 1-benzyl-4-[(3-fluorophenyl)amino]piperidine-4-carboxylate in 2.6 mL (28 mmol) acetic anhydride (neat) was heated to 120° C. for 20 hr, then poured into 50 mL of a 1:1 mixture of water and concentrated NH4OH, extracted with 100 mL EtOAc, washed with water then brine, dried over MgSO4, filtered, and concentrated. Purification by automated flash chromatography (40 g silica gel cartridge 0-5% MeOH/CH2Cl2) over 15 min) afforded ethyl 4-[acetyl(3-fluorophenyl)amino]-1-benzylpiperidine-4-carboxylate. 1H NMR (CDCl3, 400 MHz) δ 7.39 (m, 1H); 7.20-7.31 (m, 4H); 7.06-7.15 (m, 4H); 4.25 (q, J=7.14 Hz, 2H); 3.46 (s, 2H); 2.59 (br m, 2H); 2.30-2.48 (m, 3H); 2.22 (m, 2H); 1.72 (s, 3H) 1.63 (m, 2H); 1.31 (t, J=7.15, 3H). Electrospray mass spectrum M+H=399.2

Workup

  1. extractionextracted with 100 mL EtOAc
  2. washwashed with water
  3. dry with materialbrine, dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by automated flash chromatography (40 g silica gel cartridge 0-5% MeOH/CH2Cl2) over 15 min)

Sources & evidence

ORD record
ord-64b98fdffe4547ac8ddb13f38a0c2658
Source dataset
uspto-grants-2012_02
Patent number
US08114887B2

Reaction notes

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