Acetone → HCID 59640565, compound

HRID 2250133Notes

Reaction equation

HRID 2250133 reaction equation
Cl.Cl.[CH3:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][N:5]1[CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH2:20][NH:19][CH2:18][CH2:17]2.[CH3:24][C:25]([CH3:27])=O.[BH3-]C#N.[Na+]>CO.O>[CH:25]([N:19]1[CH2:18][CH2:17][C:16]2[C:21](=[CH:22][CH:23]=[C:14]([O:13][CH2:12][CH2:11][CH2:10][N:5]3[CH2:6][CH2:7][CH2:8][CH2:9][CH:4]3[CH3:3])[CH:15]=2)[CH2:20]1)([CH3:27])[CH3:24]

Participants

6

Reactant 3

HCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 69311484HCID 69311484, compound

Product 1

HCID 59640565HCID 59640565, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a flask equipped with a stir bar is placed 6-[3-(2-Methyl-piperidin-1-yl)-propoxy]-1,2,3,4-tetrahydro-isoquinoline dihydrochloride (300 mg, 0.83 mmol), acetone (excess), NaCNBH3 (155 mg, 2.5 mmol) in MeOH (8 mL) and the mixture stirred at room temperature for 2 h. The reaction mixture is diluted with water, and extracted with CH2Cl2. The organic phase is dried over Na2SO4 and concentrated. M+1 331, LCMS >98% @ 230 nm and ELSD.

Workup

  1. customTo a flask equipped with a stir bar
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic phase is dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0765d2e139b14b3291263e9bcc8ca943
Source dataset
uspto-grants-2008_01
Patent number
US07314937B2

Reaction notes

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