Sodium Bicarbonate → (9H-fluoren-9-yl)methyl 4-(2-phenylthiazol-4-yl)piperidine-1-carboxylate

HRID 522863Notes

Reaction equation

HRID 522863 reaction equation
Br[CH2:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][CH:15]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:21]3[C:16]2=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:12])[CH2:7][CH2:6]1)=O.[C:28]([NH2:36])(=[S:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])(O)=O.[Na+]>CCO>[C:29]1([C:28]2[S:35][CH:2]=[C:3]([CH:5]3[CH2:6][CH2:7][N:8]([C:11]([O:13][CH2:14][CH:15]4[C:27]5[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=5[C:21]5[C:16]4=[CH:17][CH:18]=[CH:19][CH:20]=5)=[O:12])[CH2:9][CH2:10]3)[N:36]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 683563ThiobenzamideHCID 86685241(9H-fluoren-9-yl)methyl 4-(bromoacetyl)piperidine-1-carboxylate

Product 1

HCID 67353898(9H-fluoren-9-yl)methyl 4-(2-phenylthiazol-4-yl)piperidine-1-carboxylateYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of (9H-fluoren-9-yl)methyl 4-(bromoacetyl)piperidine-1-carboxylate (3 g, 7.03 mmol) in EtOH (20 mL) was added thiobenzamide (0.96 g, 7.03 mmol). This reaction mixture was stirred at RT for 24 h. NaHCO3 (3 g) was added and the reaction mixture was further stirred for 5 d. The reaction mixture was concentrated to afford the crude material which was chromatographed over silica gel eluting with a gradient (0-10% EtOAc:hexanes) to afford (9H-fluoren-9-yl)methyl 4-(2-phenylthiazol-4-yl)piperidine-1-carboxylate (2 g, 61%) as an off white solid.

Workup

  1. stirringthe reaction mixture was further stirred for 5 d
  2. concentrationThe reaction mixture was concentrated
  3. customto afford the crude material which
  4. customwas chromatographed over silica gel eluting with a gradient (0-10% EtOAc:hexanes)

Sources & evidence

ORD record
ord-fec98cb7b66744eb92fa19de0b0b8e70
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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