Hydrochloric Acid → 3-Amino-propyl-4,4-diphenyl piperidine

HRID 322110Notes

Reaction equation

HRID 322110 reaction equation
[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]#[N:16])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[OH-].[Na+]>C1COCC1>[NH2:16][CH2:15][CH2:14][CH2:13][N:10]1[CH2:11][CH2:12][C:7]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 155128643-(4,4-Diphenylpiperidin-1-yl)propionitrile

Product 1

HCID 101085183-Amino-propyl-4,4-diphenyl piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3-(4,4-diphenylpiperidin-1-yl)propionitrile (2.00 g, 6.89 mmol, 1.0 equiv) in anhydrous THF (20 mL) under argon was added a solution of BH3 in THF (1.0M, 24.1 mL, 24 mmol, 3.5 equiv) at room temperature. The mixture was refluxed for 4.5 hours and then cooled to room temperature. Aqueous HCl (6N, 50 mL) was added and stirring was continued for 1 hour. The mixture was basified to pH 9 by addition of 6N aq. NaOH, extracted 3 times with CH2Cl2, dried over MgSO4 and concentrated.

Workup

  1. temperatureThe mixture was refluxed for 4.5 hours
  2. extractionextracted 3 times with CH2Cl2
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-82cc242c23404d548505ceb9b2bc568d
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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