Diisopropylcarbodiimide → N-methyl-3-phenyl-N-(1-(thiazol-2-yl)piperidin-4-yl)propiolamide

HRID 1880653Notes

Reaction equation

HRID 1880653 reaction equation
CC(C)N=C=NC(C)C.[CH3:10][NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][CH:20]=[CH:21][N:22]=2)[CH2:14][CH2:13]1.[C:23]1([C:29]#[C:30][C:31](O)=[O:32])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CC#N>[CH3:10][N:11]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][CH:20]=[CH:21][N:22]=2)[CH2:14][CH2:13]1)[C:31](=[O:32])[C:30]#[C:29][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 69475Phenylpropiolic AcidHCID 20782514N-methyl-1-(thiazol-2-yl)piperidin-4-amine

Product 1

HCID 23649205N-methyl-3-phenyl-N-(1-(thiazol-2-yl)piperidin-4-yl)propiolamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

685 μl (4.38 mmol) DIC was added to a solution of 785 mg (4.00 mmol) N-methyl-1-(thiazol-2-yl)piperidin-4-amine and 640 mg (4.38 mmol) 3-phenyl-propiolic acid in MeCN (40 ml) and the reaction solution was stirred for 3 h at RT. Subsequently, concentration took place in vacuo and the residue was taken up by chloroform, washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. 421 mg (1.30 mmol, 32%) (N-methyl-3-phenyl-N-(1-(thiazol-2-yl)piperidin-4-yl)propiolamide was obtained by CC (SiO2, 1.DCE 2.Chloroform). MS [MH+] 326.1

Workup

  1. concentrationSubsequently, concentration
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-adf8f588b0424f14af75f83fa9112c1b
Source dataset
uspto-grants-2012_11
Patent number
US08318774B2

Reaction notes

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