Ethylamine hydrochloride → HCID 22278836, compound

HRID 1063299Notes

Reaction equation

HRID 1063299 reaction equation
[OH-].[K+].Cl.[CH2:4]([NH2:6])[CH3:5].[CH2:7]([N:14]1[CH2:19][CH2:18][C:17](=O)[C:16]([CH3:22])([CH3:21])[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C([BH3-])#N.[Na+]>CO>[CH2:7]([N:14]1[CH2:19][CH2:18][CH:17]([NH:6][CH2:4][CH3:5])[C:16]([CH3:22])([CH3:21])[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 11198Ethylamine hydrochlorideHCID 14797Potassium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 97944131-Benzyl-3,3-dimethylpiperidin-4-one

Product 1

HCID 22278836HCID 22278836, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium hydroxide (4.6 g, 83.0 mmol) was added to the stirred solution of ethylamine hydrochloride (6.8 g, 83.0 mmol) in methanol (70 ml) and stirring was continued for 30 min at 30° C. 1-benzyl-3,3-dimethyl-4-piperidone (3.5 g, 16.6 mmol)), was added to the resulting mixture and stirred for 6 hr. Sodium cyanoborohydride (1.0 g, 16.6 mmol) was added to it and reaction mixture was stirred for 15 hr. The reaction mixture was concentrated to dryness, triturated with water, extracted with chloroform, dried (Na2SO4) and concentrated to give 1-benzyl-4-ethylamino-3,3-dimethylpiperidine. Yield 3.8 g (88%), C16H26N2, m/z 247 (M+1), PMR (CDCl3): 0.9 (s, 3H), 1.06 (s, 3H), 1.18-1.38 (m, 5H), 1.64-2.8 (m, 6H), 2.94 (m, 1H), 3.44 (dd, 2H), 7.2 (m, 5H).

Workup

  1. stirringstirred for 6 hr
  2. stirringwas stirred for 15 hr
  3. concentrationThe reaction mixture was concentrated to dryness
  4. customtriturated with water
  5. extractionextracted with chloroform
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-abb244ae254b4318860ada1fc60dfd2c
Source dataset
uspto-grants-2005_11
Patent number
US06964966B2

Reaction notes

Loading…