Hydrochloric Acid → 3-(2-isopropylaminopropyl)-4-(4-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone hydrochloride hemihydrate

HRID 26427Notes

Reaction equation

HRID 26427 reaction equation
[CH2:1]([C:5]1[C:6](=[O:20])[NH:7][CH2:8][CH2:9][CH2:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:2]([CH3:4])=[O:3].[CH:21]([NH2:24])([CH3:23])[CH3:22].[ClH:25].C([BH3-])#N.[Na+]>CO>[OH2:3].[ClH:25].[CH:21]([NH:24][CH:2]([CH3:4])[CH2:1][C:5]1[C:6](=[O:20])[NH:7][CH2:8][CH2:9][CH2:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)([CH3:23])[CH3:22].[CH:21]([NH:24][CH:2]([CH3:4])[CH2:1][C:5]1[C:6](=[O:20])[NH:7][CH2:8][CH2:9][CH2:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)([CH3:23])[CH3:22].[ClH:25]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6363IsopropylamineHCID 5003444Sodium cyanoborohydrideHCID 20332955HCID 20332955, compound

Product 1

HCID 705953463-(2-isopropylaminopropyl)-4-(4-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone hydrochloride hemihydrate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solution of 13.6 g of 3-acetonyl-4-(4-methoxyphenyl)-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 three days. The mixture is cooled to 0°, acidified to pH=1 with concentrated hydrochloric acid and evaporated. The residue is taken up in water, the mixture washed with diethyl ether, rendered basic to pH=10-11 with 3 N aqueous sodium hydroxide and extracted with diethyl ether. The extract is dried, evaporated and 13.5 g of the residual free base is dissolved in 80 ml of acetone. The solution is treated with 10.5 ml of 4.4 N ethanolic hydrochloric acid, the mixture evaporated, the residue crystallized from diethyl ether and recrystallized from isopropanol-ethyl acetate, to yield the 3-(2-isopropylaminopropyl)-4-(4-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone hydrochloride hemihydrate melting at 165°-167°.

Workup

  1. temperatureThe mixture is cooled to 0°
  2. customevaporated
  3. washthe mixture washed with diethyl ether
  4. extractionextracted with diethyl ether
  5. customThe extract is dried
  6. customevaporated
  7. dissolution13.5 g of the residual free base is dissolved in 80 ml of acetone
  8. additionThe solution is treated with 10.5 ml of 4.4 N ethanolic hydrochloric acid
  9. customthe mixture evaporated
  10. customthe residue crystallized from diethyl ether
  11. customrecrystallized from isopropanol-ethyl acetate

Sources & evidence

ORD record
ord-39a13a7f23354cbcb1053764852857cf
Source dataset
uspto-grants-1979_04
Patent number
US04150129

Reaction notes

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