Water → HCID 11374413, compound

HRID 1434560Notes

Reaction equation

HRID 1434560 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][CH:15]([C:18](O)=[O:19])[CH2:14][CH2:13]1.ON1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2N=N1.Cl.CN(C)[CH2:34][CH2:35][CH2:36][N:37]=C=NCC.O.CN(C)[CH:46]=[O:47]>>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:13][CH2:14][CH:15]([C:18]([NH:37][C:36]2[C:35]3[CH2:34][C@@H:46]([OH:47])[CH2:28][CH2:29][C:30]=3[CH:25]=[CH:26][CH:27]=2)=[O:19])[CH2:16][CH2:17]1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57936052HCID 57936052, compound

Product 1

HCID 11374413HCID 11374413, compoundYield 28%

Procedure

1-(2-Chlor-4-trifluoromethylphenyl)-piperidine-4-carboxylic acid (0.36 g, 1.16 mmol), (7S)-7-hydroxy-5,6,7,8-tetahydronaphthaleneamine (0.17 g, 1.05 mmol), 1-hydroxy-1H-benzotriazole (0.17 g, 126 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.26 g, 1.37 mmol) were combined in 10 ml of N,N-dimethylformamide under an argon atmosphere and stirred at room temperature overnight Water was added and the mixture was extracted with ethyl acetate three times. The combined organic phases were dried over magnesium sulfate, evaporated under reduced pressure, and the residue was separated over silica gel in ethyl acetate. Additional purification was achieved by preparative RP-HPLC using a water/acetonitrile gradient, yielding 1-[2-chloro-4-(trifluoromethyl)phenyl]-N-[(7S)-7-hydroxy-5,6,7,8-tetrahydro-naphthalen-1-yl]piperidine-4-carboxamide (0.132 g, 28% yield).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate three times
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customthe residue was separated over silica gel in ethyl acetate
  6. customAdditional purification

Sources & evidence

ORD record
ord-5cef627a665444d8be044e75d4f7a82f
Source dataset
uspto-grants-2009_11
Patent number
US07615557B2

Reaction notes

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