Hydrochloric Acid → 2-((1,2,3,6-Tetrahydropyridin-4-yl)methyl)thiazole hydrochloride

HRID 2175736Notes

Reaction equation

HRID 2175736 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][C:7]1[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH:8]=1.[ClH:20]>C(Cl)Cl.C(OCC)C>[ClH:20].[NH:10]1[CH2:9][CH:8]=[C:7]([CH2:6][C:2]2[S:1][CH:5]=[CH:4][N:3]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 89610024tert-butyl 4-(thiazol-2-ylmethyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 904115082-((1,2,3,6-Tetrahydropyridin-4-yl)methyl)thiazole hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
27.5 °C

Procedure

To a stirred solution of tert-butyl 4-(thiazol-2-ylmethyl)-5,6-dihydropyridine-1(2H)-carboxylate (F) (1.5 g, 5.36 mmol) in CH2Cl2 (20 mL) was added 2M HCl in diethyl ether (5 mL) dropwise at 0° C. and the reaction mixture was allowed to stir at 20-35° C. for 2 h. Then the reaction mixture was rotary evaporated under vacuum to get the desired compound as a brown liquid (1.6 g); 1H NMR (400 MHz, DMSO-d6) δ 9.23 (bs, 2H), 7.77 (d, J=2.5 Hz, 1H), 7.68 (d, J=3.2 Hz, 1H), 5.61 (s, 1H), 3.80 (s, 2H), 3.58-3.54 (m, 2H), 3.15-3.11 (m, 2H), 2.27-2.23 (m, 2H).

Workup

  1. customThen the reaction mixture was rotary evaporated under vacuum

Sources & evidence

ORD record
ord-b06570961ed046deb811656223cb7a61
Source dataset
uspto-grants-2015_06
Patent number
US09062075B2

Reaction notes

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