Potassium Carbonate → Tert-butyl (1-(thiazol-2-yl)piperidin-4-yl)carbamate

HRID 1880649Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[S:9][CH:10]=[CH:11][N:12]=1.[C:13]([O:17][C:18](=[O:26])[NH:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([CH3:16])([CH3:15])[CH3:14]>CN(C=O)C>[C:13]([O:17][C:18](=[O:26])[NH:19][CH:20]1[CH2:25][CH2:24][N:23]([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)[CH2:22][CH2:21]1)([CH3:16])([CH3:14])[CH3:15]

Participants

Conditions

Temperature: 120 °C

Procedure

6.91 g (75.0 mmol) potassium carbonate was added to a solution of 1.35 ml (15.0 mmol) 2-bromothiazole and 3.00 g (15.0 mmol) piperidin-4-yl-carbamic acid-tert-butyl ester in DMF (50 ml) and heated to 120° C. for 8 h. Subsequently, the solvent was removed in vacuo and the residue taken up by chloroform. This solution was washed with water and brine in turn, dried over MgSO4, filtered and concentrated in vacuo. Column chromatography (SiO2, chloroform) was carried out on the residue, yielding 1.14 g (4.0 mmol, 27%) (1-thiazol-2-yl-piperidin-4-yl)-carbamic acid-tert-butyl ester.

Workup

customSubsequently, the solvent was removed in vacuo
washThis solution was washed with water and brine in turn
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ae19b9e5b73b439b9469dc005af7fd53
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318774B2

Reaction notes

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