Ammonium Hydroxide → 6,7,8,9,10,11-Hexahydro-3-Methoxy-5-Methyl-5,10-Methano-5H-Benzocyclononen-12-Amine

HRID 2072164Notes

Reaction equation

HRID 2072164 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]2[CH2:7][CH:8]3[C:14](=O)[C:13]([CH3:16])([C:5]=2[CH:4]=1)[CH2:12][CH2:11][CH2:10][CH2:9]3.[OH-].[NH4+:20].[H][H]>[Ni].C(O)C>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]2[CH2:7][CH:8]3[CH:14]([NH2:20])[C:13]([CH3:16])([C:5]=2[CH:4]=1)[CH2:12][CH2:11][CH2:10][CH2:9]3

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 214101236,7,8,9,10,11-hexahydro-3-methoxy-5-methyl-5,10-methano-5H-benzocyclononen 12-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 214100706,7,8,9,10,11-Hexahydro-3-Methoxy-5-Methyl-5,10-Methano-5H-Benzocyclononen-12-Amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

6,7,8,9,10,11-Hexahydro-3-methoxy-5-methyl-5,10-methano-5H-benzocyclononen-12-one, oxime (15 g. 0.058 m.) Raney nickel (3 tsps.) ethanol (100 ml.) and concentrated ammonium hydroxide (50 ml.) are shaken with hydrogen at 45 psi and 45° C. The catalyst is removed by filtration and the filtrate concentrated to remove solvent. The residue is distilled under reduced pressure to afford the title product (11 g.), b.p. 140°-142° C. (0.2 mm.) HCl salt, m.p. 298°-299° C.

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate concentrated
  3. customto remove solvent
  4. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-d181444474e54cc3a72cbae5c3ba9ea0
Source dataset
uspto-grants-1977_09
Patent number
US04049701

Reaction notes

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