Triethylamine → N-[3-(3,5-bis(trifluoromethyl)benzyloxy)-2-phenylpropyl]-1-methylpiperidine-4-carboxamide

HRID 548199Notes

Reaction equation

HRID 548199 reaction equation
C[C:2]1([C:8]([OH:10])=O)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl.[F:12][C:13]([F:37])([F:36])[C:14]1[CH:15]=[C:16]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:17][O:18][CH2:19][CH:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:21][NH2:22].[CH2:38](N(CC)CC)C.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.O>[F:12][C:13]([F:36])([F:37])[C:14]1[CH:15]=[C:16]([CH:29]=[C:30]([C:32]([F:34])([F:33])[F:35])[CH:31]=1)[CH2:17][O:18][CH2:19][CH:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:21][NH:22][C:8]([CH:2]1[CH2:3][CH2:4][N:5]([CH3:38])[CH2:6][CH2:7]1)=[O:10]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 221045794-Methylpiperidine-4-carboxylic acidHCID 866240403-(3,5-Bis(trifluoromethyl)benzyloxy)-2-phenylpropylamine hydrochloride

Product 1

HCID 86624039N-[3-(3,5-bis(trifluoromethyl)benzyloxy)-2-phenylpropyl]-1-methylpiperidine-4-carboxamideYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-Methylpiperidine-4-carboxylic acid (0.41 g, 2.9 mmol), the compound produced in Example 17 (0.99 g, 2.9 mmol) and triethylamine (0.40 mL, 2.9 mmol) were dissolved in CH2Cl2 (10 mL) and WSC.HCl (0.56 g, 2.9 mmol) was added thereto at room temperature. After the mixture was stirred for 20 hours at room temperature, water was added to the residue obtained by evaporation of the solvent in vacuo and the mixture was extracted with ethyl acetate. The organic layers were combined, washed with water and a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was evaporated therefrom in vacuo to give Compound 1 (1.12 g, 93%) as an oily product.

Workup

  1. customat room temperature
  2. customobtained by evaporation of the solvent in vacuo
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materiala saturated saline solution and dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-46867278d280445aa02087d1d2a66153
Source dataset
uspto-grants-2011_05
Patent number
US07939552B2

Reaction notes

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