2,2-Diphenylbutyric acid → 2,2-diphenyl-N-(3-{4-[3-(propionylamino)phenyl]-1-piperidinyl}propyl)butanamide

HRID 1269193Notes

Reaction equation

HRID 1269193 reaction equation
[C:1]1([C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:11][CH3:12])[C:8](O)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:19][CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([C:29]2[CH:30]=[C:31]([NH:35][C:36](=[O:39])[CH2:37][CH3:38])[CH:32]=[CH:33][CH:34]=2)[CH2:25][CH2:24]1>>[C:13]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([CH2:11][CH3:12])[C:8]([NH:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([NH:35][C:36](=[O:39])[CH2:37][CH3:38])[CH:30]=3)[CH2:25][CH2:24]2)=[O:9])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 779022,2-Diphenylbutyric acidHCID 21957142N-{3-[1-(3-aminopropyl)4-piperidinyl]phenyl}propanamide

Product 1

HCID 219571492,2-diphenyl-N-(3-{4-[3-(propionylamino)phenyl]-1-piperidinyl}propyl)butanamide

Procedure

Example 15 was prepared from 2,2-diphenylbutanoic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}propanamide according to the procedures described in Scheme 10: 1H NMR (400 MHz, CDCl3) δ 7.43–7.38 (m, 1H), 7.37–7.29 (m, 9H), 7.28–7.21 (m, 4H), 6.90 (d, 1H, J=8.2 Hz), 6.43 (t, 1H, J=4.1), 3.32 (q, 2H, J=6.5 Hz), 2.95–2.89 (m, 2H), 2.45 (q, 2H, J=7.9 Hz), 2.43–2.35 (m, 3H), 2.27 (t, 2H, J=6.5 Hz), 2.01–1.92 (m, 2H), 1.78–1.59 (m, 6H), 1.24 (t, 3H, J=7.9 Hz), 0.79 (t, 3H, J=6.5 Hz); ESMS m/e: 512.3 (M+H)+.

Sources & evidence

ORD record
ord-a7a3375b64df4b3fa259119bbc429522
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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