Water → 2-[4-(Aminomethyl)piperidin-1-yl]ethan-1-ol

HRID 1483800Notes

Reaction equation

HRID 1483800 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]#[N:11])[CH2:6][CH2:5]1.S(C)C.O.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[NH2:11][CH2:10][CH:7]1[CH2:6][CH2:5][N:4]([CH2:3][CH2:2][OH:1])[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 1068Dimethyl SulfideHCID 11430Potassium CarbonateHCID 138231551-(2-Hydroxyethyl)piperidine-4-carbonitrile

Product 1

HCID 73304762-[4-(Aminomethyl)piperidin-1-yl]ethan-1-olYield 47.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of compound 1-(2-hydroxyethyl)piperidine-4-carbonitrile (300 mg, 2 mmol) in dry THF (5 mL) at 0° C., BH3.SMe2 (220 mg, 2.4 mmol) was added dropwise. The mixture was stirred at 0° C. for 2 hrs. Water was added then K2CO3. The mixture was filtered and concentrated to give compound 2-(4-(aminomethyl)piperidin-1-yl)ethanol (150 mg, 47%).

Workup

  1. customat 0° C.
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6305663d1f8f42548e4053b3e2985a2f
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

Loading…