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

HRID 507287Notes

Reaction equation

HRID 507287 reaction equation
Br.[C:2]1([C:8]2[N:9]=[C:10]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[S:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][C:20]([CH3:22])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>C1COCC1.C(O)(=O)C.CCN(CC)CC.CO>[CH:20]([N:16]1[CH2:17][CH2:18][CH:13]([C:10]2[S:11][CH:12]=[C:8]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[N:9]=2)[CH2:14][CH2:15]1)([CH3:22])[CH3:19]

Participants

9

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 684624534-(4-Phenyl-thiazol-2-yl)-piperidine hydrobromide

Product 1

HCID 160618524-(4-Phenyl-1,3-thiazol-2-yl)-1-(propan-2-yl)piperidine

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 24.5 mg (0.1 mmol) 4-(4-phenyl-thiazol-2-yl)-piperidine hydrobromide, excess acetone and excess sodium triacetoxyborohydride in 1 ml THF and 20 μl acetic acid was stirred at room temperature for 16 h. After addition of 0.2 ml water, 0.2 ml methanol and 0.15 ml NEt3 the mixture was purified by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water (0.1% NEt3) to yield after evaporation of the product fractions 12.8 mg (45 %) of the title compound. (m/e): 287.3 (MH+; 100%).

Workup

  1. customwas purified by preparative HPLC on reversed phase
  2. washeluting with a gradient of acetonitrile/water (0.1% NEt3)
  3. customto yield
  4. customafter evaporation of the product fractions 12.8 mg (45 %) of the title compound

Sources & evidence

ORD record
ord-32ad9ade040f44338dde7f120d64dc4b
Source dataset
uspto-grants-2010_08
Patent number
US07786143B2

Reaction notes

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