Hydrochloric Acid → 4-(3-Amino-phenyl)-pipendine-1-carboxylic acid 4-(5-trifluoromethyl-pyridin2-yloxy)-phenyl Ester

HRID 1831450Notes

Reaction equation

HRID 1831450 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Cl.Cl[C:16]([O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][N:27]=2)=[CH:21][CH:20]=1)=[O:17]>ClCCl.CN(C)C=O.C(OCC)(=O)C>[F:34][C:32]([F:33])([F:35])[C:29]1[CH:30]=[CH:31][C:26]([O:25][C:22]2[CH:23]=[CH:24][C:19]([O:18][C:16]([N:11]3[CH2:12][CH2:13][CH:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([NH2:1])[CH:3]=4)[CH2:9][CH2:10]3)=[O:17])=[CH:20][CH:21]=2)=[N:27][CH:28]=1

Participants

7

Reactant 3

HCID 313Hydrochloric Acid2×HCID 220477624-(5-Trifluoromethylpyridin-2-yloxy)-phenyl chloroformateHCID 220479094-(3-Aminophenyl)piperidine

Product 1

HCID 695196114-(3-Amino-phenyl)-pipendine-1-carboxylic acid 4-(5-trifluoromethyl-pyridin2-yloxy)-phenyl Ester

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title product was prepared from 4-(3-aminophenyl)piperidine (released form the correspondent hydrochloride by a standard procedure) and 4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl chloroformate, preparative HPLC (method C) (reaction performed in a mixture of dichloromethane and dimethylformamide, 5:3). 1.7 M HCl in ethyl acetate was added to the pooled fractions containing the title product, and the fractions was evaporated to dryness (7%, light yellow solid). HPLC-MS m/z=(M+1) 458.0, Rt: 3.09 min.

Workup

  1. customreaction
  2. customthe fractions was evaporated to dryness (7%, light yellow solid)

Sources & evidence

ORD record
ord-14da6e52b9b3472b8d69b96881edf935
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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