Diketene → N-[3-(4,4-Diphenyl-piperidin-1-yl)-propyl]-3-oxo-butyramide

HRID 1956401Notes

Reaction equation

HRID 1956401 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[NH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][C:14]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][CH2:12]1>C1(C)C=CC=CC=1>[C:17]1([C:14]2([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:13][CH2:12][N:11]([CH2:10][CH2:9][CH2:8][NH:7][C:4](=[O:5])[CH2:3][C:2]([CH3:1])=[O:6])[CH2:16][CH2:15]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 12661DiketeneHCID 101085183-Amino-propyl-4,4-diphenyl piperidine

Product 1

HCID 10362296N-[3-(4,4-Diphenyl-piperidin-1-yl)-propyl]-3-oxo-butyramideYield 78.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Diketene (0.44 mL, 5.68 mmol, 1.3 equiv, Aldrich) was added at room temperature to a stirred solution of 1-(3-aminopropyl)-4-,4-diphenylpiperidine (1.288 g, 4.37 mmol, 1.0 equiv) in anhydrous toluene (15 mL) under argon, and stirring was continued for 48 hours. The mixture was concentrated to give 1.294 g (78%) of white solid, which was used for the next reaction without purification: 1H NMR (300 MHz, CDCl3) δ 1.70 (tt, J=6.4, 6.4 Hz, 2H), 2.23 (s, 3H), 2.44 (br t, J=6.5 Hz), 2.49-2.67 (m, 8H), 3.32 (br t, J=5.8 Hz), 3.36 (s, 2H), 7.16 (m, 2H), 7.27 (m, 8H).

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-be9bbfdb31934c728f6246ce9b213b12
Source dataset
uspto-grants-1998_07
Patent number
US05780485

Reaction notes

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