Triethylamine → 3-[(Phenylcarbonyl)amino]-N-(tetrahydrofuran-2-ylmethyl)-5-[4-(trifluoromethyl)phenyl]piperidine-1-carboxamide

HRID 876336Notes

Reaction equation

HRID 876336 reaction equation
C([C:3]1[CH:27]=[CH:26][CH:25]=[CH:24][C:4]=1[C:5]([NH:7][CH:8]1[CH2:13][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH2:11][NH:10][CH2:9]1)=[O:6])C.[N:28]([CH2:31][CH:32]1[CH2:36][CH2:35][CH2:34][O:33]1)=[C:29]=[O:30].C(N(CC)CC)C>C1COCC1>[C:4]1([C:5]([NH:7][CH:8]2[CH2:13][CH:12]([C:14]3[CH:15]=[CH:16][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:18][CH:19]=3)[CH2:11][N:10]([C:29]([NH:28][CH2:31][CH:32]3[CH2:36][CH2:35][CH2:34][O:33]3)=[O:30])[CH2:9]2)=[O:6])[CH:24]=[CH:25][CH:26]=[CH:27][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 184675172-(Isocyanatomethyl)oxolaneHCID 66701258ethyl-N-{5-[4-(trifluoromethyl)phenyl]piperidin-3-yl}benzamide

Product 1

HCID 667015263-[(Phenylcarbonyl)amino]-N-(tetrahydrofuran-2-ylmethyl)-5-[4-(trifluoromethyl)phenyl]piperidine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

80 mg (0.23 mmol) of ethyl-N-{5-[4-(trifluoromethyl)phenyl]piperidin-3-yl}benzamide were initially charged in 2 ml of THF, and 29 mg (0.23 mmol) of 2-(isocyanatomethyl)tetrahydrofuran and 35 μl (0.25 mmol) of triethylamine were added. The mixture was stirred at RT overnight. The reaction mixture was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 88 mg (81% of theory)

Workup

  1. customThe reaction mixture was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient)

Sources & evidence

ORD record
ord-d8691db52196442faf14f6edeac930dd
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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