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

HRID 1105542Notes

Reaction equation

HRID 1105542 reaction equation
O=[C:2]([CH3:23])[CH2:3][C:4]1[C:5](=[O:22])[N:6]([CH3:21])[CH2:7][CH2:8][CH:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=3)[C:10]=12.[CH:24]([NH2:27])([CH3:26])[CH3:25].Cl.C([BH3-])#N.[Na+]>CO>[CH:24]([NH:27][CH:2]([CH3:23])[CH2:3][C:4]1[C:5](=[O:22])[N:6]([CH3:21])[CH2:7][CH2:8][CH:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=3)[C:10]=12)([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6363IsopropylamineHCID 5003444Sodium cyanoborohydride2×HCID 205556151-(2-oxopropyl)-9-methoxy-3-methyl-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

Product 1

HCID 205555861-(2-isopropylaminopropyl)-9-methoxy-3-methyl-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of 4.7 g of 1-(2-oxopropyl)-9-methoxy-3-methyl-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one, 8.88 ml of isopropylamine, 3.45 ml of 5 N methanolic hydrochloric acid, 1.02 g of sodium cyanoborohydride and 75 ml of methanol is stirred and refluxed overnight. An additional 1.02 g of sodium cyanoborohydride is added and refluxing is continued for another day. The mixture is cooled, acidified to pH=1 with concentrated hydrochloric acid, the methanol is evaporated and the solution washed with diethyl ether. It is rendered basic to pH=10-11 with 3 N aqueous sodium hydroxide, extracted with diethyl ether, the extract dried and evaporated. The residue is recrystallized from hexane, to yield the 1-(2-isopropylaminopropyl)-9-methoxy-3-methyl-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one melting at 118°-120°.

Workup

  1. temperaturerefluxed overnight
  2. temperaturerefluxing
  3. waitis continued for another day
  4. temperatureThe mixture is cooled
  5. customthe methanol is evaporated
  6. washthe solution washed with diethyl ether
  7. extractionextracted with diethyl ether
  8. customthe extract dried
  9. customevaporated
  10. customThe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-2822d0ff10c94436bf1a47d0a1f11169
Source dataset
uspto-grants-1982_01
Patent number
US04309345

Reaction notes

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