Phenylpropiolic Acid → 3-phenyl-N-(1-(thiazol-2-yl)piperidin-4-yl)propiolamide

HRID 1880651Notes

Reaction equation

HRID 1880651 reaction equation
FC(F)(F)C(O)=O.[S:8]1[CH:12]=[CH:11][N:10]=[C:9]1[N:13]1[CH2:18][CH2:17][CH:16]([NH2:19])[CH2:15][CH2:14]1.[C:20]1([C:26]#[C:27][C:28](O)=[O:29])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCN(C(C)C)C(C)C>ClCCCl>[C:20]1([C:26]#[C:27][C:28]([NH:19][CH:16]2[CH2:17][CH2:18][N:13]([C:9]3[S:8][CH:12]=[CH:11][N:10]=3)[CH2:14][CH2:15]2)=[O:29])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 69475Phenylpropiolic AcidHCID 81531DiisopropylethylamineHCID 691528731-(Thiazol-2-yl)piperidin-4-amine trifluoroacetate

Product 1

HCID 236492043-phenyl-N-(1-(thiazol-2-yl)piperidin-4-yl)propiolamideYield 51.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 500 mg (1.68 mmol) 1-(thiazol-2-yl)piperidin-4-amine trifluoroacetate, 332 mg (2.02 mmol) 3-phenylpropiolic acid and 1.17 ml DIPEA in DCE (20 ml) was stirred for 5 h at RT. Subsequently, the reaction solution was washed with water and a sat. aqueous Na2CO3 soln and dried over MgSO4. After filtering and concentration in vacuo, column chromatography (SiO2, chloroform) was performed on the residue, yielding 267 mg (0.86 mmol, 51%) 3-phenyl-N-(1-(thiazol-2-yl)piperidin-4-yl)propiolamide. MS [MH+] 312.1

Workup

  1. washSubsequently, the reaction solution was washed with water
  2. dry with materiala sat. aqueous Na2CO3 soln and dried over MgSO4
  3. filtrationAfter filtering
  4. concentrationconcentration in vacuo, column chromatography (SiO2, chloroform)

Sources & evidence

ORD record
ord-2c1ff923552146468afc4db129fcd779
Source dataset
uspto-grants-2012_11
Patent number
US08318774B2

Reaction notes

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