2-Amino-2-methylpropionitrile → hexahydro-1H-pyrrolizine-7a-carbonitrile

HRID 330593

Reaction equation

HRID 330593 reaction equation
[NH2:1][C:2](C)(C)C#N.Cl[CH2:8][CH2:9][CH2:10][C:11](=O)[CH2:12][CH2:13][CH2:14]Cl.[NH3:17].CO>>[C:2]([C:11]12[CH2:12][CH2:13][CH2:14][N:17]1[CH2:8][CH2:9][CH2:10]2)#[N:1]

Participants

4

Reactant 3

HCID 880222-Amino-2-methylpropionitrileHCID 2467491,7-Dichloro-heptan-4-oneHCID 21705897Ammonia methanol

Product 1

HCID 11029899hexahydro-1H-pyrrolizine-7a-carbonitrileYield 82%

Procedure

A mixed solution of 2-amino-2-methylpropanenitrile (41.4 g, 492 mmol) and 1,7-dichloro-4-heptanone (30.0 g, 164 mmol) in 220 ml of 16% NH3 /MeOH solution was stirred for 24 hours at 20° C. The resulting reaction mixture was concentrated in vacuo to remove MeOH therefrom, added 0.1N NaOH to the residue, which was extracted with methylene chloride, and the extract was dried over anhydrous sodium sulfate, concentrated, and distilled in vacuo to afford 18.1 g of the desired compound (Yield: 82%).

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated in vacuo
  3. customto remove MeOH
  4. additionadded 0.1N NaOH to the residue, which
  5. extractionwas extracted with methylene chloride
  6. dry with materialthe extract was dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-141bd7dd0c4740a2b76f057e5fe7379d
Source dataset
uspto-grants-1990_01
Patent number
US04897495

Linked notes

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