1-(2-isopropyliminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one → 1-(2-isopropylaminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

HRID 46526Notes

Reaction equation

HRID 46526 reaction equation
[CH:1]([N:4]=[C:5]([CH3:25])[CH2:6][C:7]1[C:8](=[O:24])[NH:9][CH2:10][CH2:11][CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=3)[C:13]=12)([CH3:3])[CH3:2]>C(O)C.[Pt](=O)=O>[CH:1]([NH:4][CH:5]([CH3:25])[CH2:6][C:7]1[C:8](=[O:24])[NH:9][CH2:10][CH2:11][CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=3)[C:13]=12)([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 205555901-(2-isopropyliminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

Product 1

HCID 128324101-(2-isopropylaminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

The solution of 1 g of 1-(2-isopropyliminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one in 50 ml of ethanol is hydrogenated at room temperature and atmospheric pressure for 2 hours in the presence of 0.1 g of platinum dioxide catalyst. The mixture is filtered, the filtrate evaporated and the residue crystallized from petroleum ether, to yield the 1-(2-isopropylaminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one as a mixture of the "slow" and "fast" moving isomers, melting at 118°-126°.

Workup

  1. customis hydrogenated at room temperature
  2. filtrationThe mixture is filtered
  3. customthe filtrate evaporated
  4. customthe residue crystallized from petroleum ether

Sources & evidence

ORD record
ord-f6be3965cf9d443fbe35002d7d1ba901
Source dataset
uspto-grants-1979_11
Patent number
US04173633

Reaction notes

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