Methanol → 4-(2-Phenyl-1,3-thiazol-4-yl)piperidine

HRID 522864Notes

Reaction equation

HRID 522864 reaction equation
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([CH:12]3[CH2:17][CH2:16][N:15](C(OCC4C5C=CC=CC=5C5C4=CC=CC=5)=O)[CH2:14][CH2:13]3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.N1CCCCC1>C(Cl)Cl>[C:1]1([C:7]2[S:8][CH:9]=[C:10]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 8082PiperidineHCID 67353898(9H-fluoren-9-yl)methyl 4-(2-phenylthiazol-4-yl)piperidine-1-carboxylate

Product 1

HCID 595715844-(2-Phenyl-1,3-thiazol-4-yl)piperidineYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (9H-fluoren-9-yl)methyl 4-(2-phenylthiazol-4-yl)piperidine-1-carboxylate (2 g, 4.29 mmol) in CH2Cl2:MeOH (15:5 mL) was added piperidine (5 mL). This reaction mixture was stirred at RT for 8 h. The reaction mixture was concentrated under reduced pressure and the crude material was chromatographed over silica gel eluting with a gradient (0-10% MeOH:CH2Cl2) to afford 2-phenyl-4-(piperidin-4-yl)thiazole (1 g, 96%) as an off white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe crude material was chromatographed over silica gel eluting with a gradient (0-10% MeOH:CH2Cl2)

Sources & evidence

ORD record
ord-9e74d27a48db404d8893b1cc1a7651ce
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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