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

HRID 1105539Notes

Reaction equation

HRID 1105539 reaction equation
B#B.[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:25](=[CH:26][CH:27]=1)[C:11]1=[C:12]([CH2:18][C:19]([NH:21][CH:22]([CH3:24])[CH3:23])=O)[C:13](=[O:17])[NH:14][CH2:15][CH2:16][CH:10]1[CH2:9][CH2:8]2.Cl>O1CCCC1>[CH:22]([NH:21][CH2:19][CH2:18][C:12]1[C:13](=[O:17])[NH:14][CH2:15][CH2:16][CH:10]2[CH2:9][CH2:8][C:7]3[C:25](=[CH:26][CH:27]=[C:5]([O:4][CH3:3])[CH:6]=3)[C:11]=12)([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6328200DiboronHCID 20555608[9-methoxy-2-oxo-3,4,5,5a,6,7-hexahydro-2H-naphth-[1,2-d]azepin-1-yl]-N-isopropyl-acetamide

Product 1

HCID 128324141-(2-isopropylaminoethyl)-3,4,5,5a,6,7-hexahydro-9-methoxy-2H-naphth[1,2-d]azepin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

80 ml of 1 M diborane in tetrahydrofuran are added to the suspension of 6.8 g of [9-methoxy-2-oxo-3,4,5,5a,6,7-hexahydro-2H-naphth-[1,2-d]azepin-1-yl]-N-isopropyl-acetamide in 100 ml of tetrahydrofuran while stirring under nitrogen at 0°. After 20 hours 60 ml of 3 N hydrochloric acid are added dropwise and the mixture is refluxed for one hour. The tetrahydrofuran is distilled off under reduced pressure and the remainder is diluted with water. The resulting precipitate is filtered off and re-extracted with hot water. The aqueous filtrate is washed with diethyl ether and basified with 3 N aqueous sodium hydroxide. The suspension is extracted with methylene chloride, the extract dried, evaporated and the residue recrystallized from acetone, to yield the 1-(2-isopropylaminoethyl)-3,4,5,5a,6,7-hexahydro-9-methoxy-2H-naphth[1,2-d]azepin-2-one melting at 147°-149°.

Workup

  1. temperaturethe mixture is refluxed for one hour
  2. distillationThe tetrahydrofuran is distilled off under reduced pressure
  3. additionthe remainder is diluted with water
  4. filtrationThe resulting precipitate is filtered off
  5. extractionre-extracted with hot water
  6. washThe aqueous filtrate is washed with diethyl ether
  7. extractionThe suspension is extracted with methylene chloride
  8. customthe extract dried
  9. customevaporated
  10. customthe residue recrystallized from acetone

Sources & evidence

ORD record
ord-b8b39ca57ef343a4a513b45f4559bad4
Source dataset
uspto-grants-1982_01
Patent number
US04309345

Reaction notes

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