Cyclopropylamine → HCID 69018571, compound

HRID 1063301Notes

Reaction equation

HRID 1063301 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[C:10]([CH3:16])([CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]1([NH2:20])[CH2:19][CH2:18]1.C([BH3-])#N.[Na+]>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:20][CH:17]2[CH2:19][CH2:18]2)[C:10]([CH3:16])([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 97944131-Benzyl-3,3-dimethylpiperidin-4-one

Product 1

HCID 69018571HCID 69018571, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Benzyl-3,3-dimethyl-4-piperidone (10.0 g, 46.0 mmol), was added to the stirred solution cyclopropylamine (13.1 g, 230.0 mmol) in methanol (150 ml) and stirred for 6 hr. Sodium cyanoborohydride (2.9 g, 46.0 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. The obtained crude product was purified over silica gel column. Eluted from 5% ethyl acetate in hexane gave 1-benzyl-4-cyclopropylamino-3,3-dimethyl piperidine. Yield 8.0 g (67.3%), C17H26N2, m/z 259 (M+1), PMR (CDCl3): 0.4 (m, 2H), 0.82 (s, 3H), 1.06 (s, 3H), 1.16 (m, 2H), 1.5 (bs, 1H, D2O exchangeable), 1.7 (m, 2H), 1.9-2.95 (m, 5H), 3.3-3.6 (m, 3H), 7.22 (m, 5H).

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
  7. customThe obtained crude product
  8. customwas purified over silica gel column
  9. washEluted from 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-2324abbe09e8496b80e46b6f617973e2
Source dataset
uspto-grants-2005_11
Patent number
US06964966B2

Reaction notes

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