2,2'-Dichlorobenzilic acid → N-{3-[1-(3-{[bis(2-chlorophenyl)(hydroxy)acetyl]amino}propyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide

HRID 1269328Notes

Reaction equation

HRID 1269328 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19])([OH:12])[C:9]([OH:11])=O.[NH2:20][CH2:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH:27]([C:30]2[CH:31]=[C:32]([NH:37][C:38](=[O:42])[CH:39]([CH3:41])[CH3:40])[CH:33]=[CH:34][C:35]=2[CH3:36])[CH2:26][CH2:25]1>>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])([OH:12])[C:9]([NH:20][CH2:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH:27]([C:30]2[CH:31]=[C:32]([NH:37][C:38](=[O:42])[CH:39]([CH3:40])[CH3:41])[CH:33]=[CH:34][C:35]=2[CH3:36])[CH2:26][CH2:25]1)=[O:11]

Participants

3

Reactant 2

HCID 3290602,2'-Dichlorobenzilic acidHCID 16757468N-{3-[1-(aminopropyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide

Product 1

HCID 11758223N-{3-[1-(3-{[bis(2-chlorophenyl)(hydroxy)acetyl]amino}propyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide

Procedure

Example 158 was prepared from bis(2-chlorophenyl)(hydroxy)acetic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide according to the procedures described in Scheme 12: 1H NMR (400 MHz, CDCl3) δ 8.33 (s, 1 H), 7.43–7.18 (m, 11 H), 7.05 (d, 1 H, J=8.0 Hz), 5.03 (s, 1 H), 3.60–3.49 (m, 2 H), 3.03–2.91 (m, 2 H), 2.71–2.54 (m, 1 H), 2.54–2.37 (m, 3 H), 2.25 (s, 3 H), 2.08–1.91 (m, 2 H), 1.84–1.63 (m, 4 H), 1.63–1.50 (m, 2 H), 1.17 (d, 6 H, J=6.8 Hz); ESMS m/e: 596.3 (M+H)+.

Sources & evidence

ORD record
ord-c8e22f11a4d9416a8974fb3bfe4e0441
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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