[4-(4-Chlorophenyl)phenyl]methylamine hydrochloride → Methyl 3-[3-[N-[(4'-chlorobiphenyl-4-yl)methyl]carbamoyl]piperidin-1-yl]benzoate

HRID 602172Notes

Reaction equation

HRID 602172 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([N:11]2[CH2:19][CH2:18][CH2:17][CH:13]([C:14]([OH:16])=O)[CH2:12]2)[CH:8]=[CH:9][CH:10]=1)=[O:4].Cl.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([CH2:34][NH2:35])=[CH:30][CH:29]=2)=[CH:24][CH:23]=1>>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[CH:33]=[CH:32][C:31]([CH2:34][NH:35][C:14]([CH:13]3[CH2:17][CH2:18][CH2:19][N:11]([C:7]4[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=4)[C:3]([O:2][CH3:1])=[O:4])[CH2:12]3)=[O:16])=[CH:30][CH:29]=2)=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 17998851[4-(4-Chlorophenyl)phenyl]methylamine hydrochlorideHCID 589926191-[3-(Methoxycarbonyl)phenyl]nipecotic acid

Product 1

HCID 58992588Methyl 3-[3-[N-[(4'-chlorobiphenyl-4-yl)methyl]carbamoyl]piperidin-1-yl]benzoateYield 69.3%

Procedure

Using 1-[3-(methoxycarbonyl)phenyl]nipecotic acid (108 mg, 0.410 mmol) and (4′-chlorobiphenyl-4-yl)methylamine hydrochloride (95.0 mg, 0.374 mmol), the same procedure was followed as in Step 3a of Example 3 to give 120 mg (69%) of the desired compound as colorless crystals.

Sources & evidence

ORD record
ord-77035eaf7fac4021bce845015048bb34
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

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