4-(4-Chlorophenyl)-4-hydroxypiperidine → Benzyl 1-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

HRID 1016103Notes

Reaction equation

HRID 1016103 reaction equation
[C:1]([NH:11][CH:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2([OH:32])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1.C(NC(C(O)=O)C(C)C)(=O)C1C=CC=CC=1.Cl.ClC1C=CC(C2CCNCC2)=CC=1>>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2([OH:32])[CH2:27][CH2:28][N:29]([C:16](=[O:18])[CH:12]([NH:11][C:1](=[O:2])[O:3][CH2:4][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:13]([CH3:14])[CH3:15])[CH2:30][CH2:31]2)=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 97743N-Carbobenzoyl-DL-valineHCID 2266823-Methyl-2-(phenylformamido)butanoic acidHCID 27578434-(4-chlorophenyl)piperidine Hydrochloride

Product 1

HCID 57888886Benzyl 1-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

Procedure

Example 213 was prepared in a similar manner as described for the preparation of Example 208 with the exceptions that Cbz-DL-valine and 4-(4-chlorophenyl)-4-hydroxypiperidine were substituted for benzoyl-DL-valine and 4-(4-chlorophenyl)piperidine hydrochloride, respectively. MS found: (M+H)+=446.

Workup

  1. customExample 213 was prepared in a similar manner

Sources & evidence

ORD record
ord-9e8f2a3e1fa24d7b85482907f7d8aa2c
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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