Cyclopropylamine → HCID 22278915, compound

HRID 746887Notes

Reaction equation

HRID 746887 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[C:10]([CH2:16][CH3:17])([CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:18]1([NH2:21])[CH2:20][CH2:19]1.C([BH3-])#N.[Na+]>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:21][CH:18]2[CH2:20][CH2:19]2)[C:10]([CH2:16][CH3:17])([CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 5003444Sodium cyanoborohydrideHCID 22278904HCID 22278904, compound

Product 1

HCID 22278915HCID 22278915, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Benzyl-3-ethyl-3-methyl-4-piperidinone (4.2 g, 18.18 mmol) was added to the stirred solution cyclopropylamine (6.5 g, 115 mmol) in methanol (100 ml) and stirred for 6 hr. Sodium cyanoborohydride (1.14 g, 18.18 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 furnish crude 1-benzyl-4-cyclopropylamino-3-ethyl-3-methylpiperidine. Yield 4 g (88%), C18H28N2, m/z 273 (M+1).

Workup

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

Sources & evidence

ORD record
ord-ab53f02ea23b4680bd62a49cb122900f
Source dataset
uspto-grants-2008_07
Patent number
US07393957B2

Reaction notes

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