Potassium Carbonate → Tert-butyl 4-[(2-amino-1,3-thiazol-4-yl)methyl]piperazine-1-carboxylate

HRID 1162367Notes

Reaction equation

HRID 1162367 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[NH2:15][C:16]1[S:17][CH:18]=[C:19]([CH2:21]Cl)[N:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:15][C:16]1[S:17][CH:18]=[C:19]([CH2:21][N:11]2[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH2:12]2)[N:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)HCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 23138223Tert-butyl 4-[(2-amino-1,3-thiazol-4-yl)methyl]piperazine-1-carboxylateYield 74.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Boc-piperazine (4.67 g), 2-amino-4-chloromethylthiazole hydrochloride (WO 0190090; 5.1 g) and potassium carbonate (8.4 g) in DMF (100 ml) was mixed at 65° C. for 12 hours. The precipitated insolubles were filtered off, and then the filtrate was concentrated under reduced pressure. The residue was purified with silica gel column to obtain the title compound as a brown solid (5.6 g, 74%).

Workup

  1. filtrationThe precipitated insolubles were filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified with silica gel column

Sources & evidence

ORD record
ord-7982ec2dd6ee43a79cffe9ff0fa2e2ce
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

Loading…