Hydrochloric Acid → HCID 20332946, compound

HRID 26425Notes

Reaction equation

HRID 26425 reaction equation
[CH2:1]([C:5]1[C:6](=[O:22])[NH:7][CH2:8][CH2:9][CH2:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)[C:2]([CH3:4])=[O:3].[CH:23]([NH2:26])([CH3:25])[CH3:24].[ClH:27].C([BH3-])#N.[Na+]>CO>[OH2:3].[ClH:27].[CH:23]([NH:26][CH:2]([CH3:4])[CH2:1][C:5]1[C:6](=[O:22])[NH:7][CH2:8][CH2:9][CH2:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6363IsopropylamineHCID 5003444Sodium cyanoborohydrideHCID 20332950HCID 20332950, compound

Product 1

HCID 20332946HCID 20332946, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solution of 15.1 g of 3-acetonyl-4-(3,4-dimethoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone, 25.5 ml of isopropylamine 10 ml of 5.8 N methanolic hydrogen chloride and 3.4 g of sodium cyanoborohydride in 260 ml of methanol is refluxed for 3 days. The mixture is cooled, acidified to pH=1 with concentrated hydrochloric acid, evaporated and the residue diluted with water. It is washed with ether, basified with 3 N aqueous sodium hydroxide to pH=11 and extracted with diethyl ether. The extract is dried, evaporated and the residue dissolved in 75 ml of acetone. The solution is treated with 4.4 N ethanolic hydrogen chloride, and the precipitate collected, to yield the 3-(2-isopropylaminopropyl)-4-(3,4-dimethoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone hydrochloride monohydrate melting at 135°-138°.

Workup

  1. temperatureThe mixture is cooled
  2. customevaporated
  3. additionthe residue diluted with water
  4. washIt is washed with ether
  5. extractionextracted with diethyl ether
  6. customThe extract is dried
  7. customevaporated
  8. dissolutionthe residue dissolved in 75 ml of acetone
  9. additionThe solution is treated with 4.4 N ethanolic hydrogen chloride
  10. customthe precipitate collected

Sources & evidence

ORD record
ord-e8fb93ccc5ba4b71a9137f9c776b473f
Source dataset
uspto-grants-1979_04
Patent number
US04150129

Reaction notes

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