Hydrochloric Acid → HCID 57888658, compound

HRID 1820180Notes

Reaction equation

HRID 1820180 reaction equation
Cl.[NH2:2][C@H:3]([CH:19]([CH3:21])[CH3:20])[C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5].CCN(C(C)C)C(C)C.[C:31]([N:39]=[C:40]=[S:41])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.Cl>C(Cl)Cl>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([CH:9]2[CH2:10][CH2:11][N:6]([C:4](=[O:5])[C@H:3]([NH:2][C:40]([NH:39][C:31](=[O:38])[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[S:41])[CH:19]([CH3:21])[CH3:20])[CH2:7][CH2:8]2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 68284Benzoyl isothiocyanateHCID 81531DiisopropylethylamineHCID 67299489HCID 67299489, compound

Product 1

HCID 57888658HCID 57888658, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-2-Amino-1-(4-(4-chlorophenyl)piperidin-1-yl)-3-methylbutan-1-one hydrochloride (250 mg, 0.75 mmol) in DCM (2 mL) was added DIEA (175 μL, 1 mmol) followed by the dropwise addition of benzoylisothiocyanate (106 μL, 0.78 mmol). The reaction was stirred for 2 h at rt., acidified with 1 N aqueous HCl solution to pH 3 and then extracted with Et2O (3×10 mL). The extracts were combined, washed sequentially with sat. aqueous NaHCO3 solution (1×10 mL) and sat. aqueous NaCl solution (1×10 mL), dried (MgSO4), and the solvent removed to give (R)—N-(1-(4-(4-chlorophenyl)piperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamothioyl)benzamide (m/z, 458, M+1) as an oil (300 mg) in greater than 90% HPLC purity.

Workup

  1. extractionextracted with Et2O (3×10 mL)
  2. washwashed sequentially with sat. aqueous NaHCO3 solution (1×10 mL) and sat. aqueous NaCl solution (1×10 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed

Sources & evidence

ORD record
ord-f5db0baa3ea94914820ae8486369b9dc
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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