Ammonium Chloride → HCID 20433756, compound

HRID 1154641Notes

Reaction equation

HRID 1154641 reaction equation
[CH3:1][O:2][C:3]1[C:31]([O:32][CH3:33])=[CH:30][C:6]2[CH2:7][C:8](=O)[N:9]([CH2:12][CH2:13][CH2:14][N:15]([CH3:28])[CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=3)[CH2:10][CH2:11][C:5]=2[CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-:40].[NH4+]>CCOCC.O1CCCC1>[ClH:40].[ClH:40].[CH3:1][O:2][C:3]1[C:31]([O:32][CH3:33])=[CH:30][C:6]2[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][CH2:14][N:15]([CH3:28])[CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=3)[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 65637ZatebradineHCID 21226445Aluminium lithium hydride

Product 1

HCID 20433756HCID 20433756, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.7 gm (6 mmols) of 1-[7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-methyl-N-(2-{3,4-dimethoxy-phenyl}ethyl)-amino]-propane were dissolved in 100 ml of absolute ether and 100 ml of absolute tetrahydrofuran; the solution was mixed with 0.25 gm of lithium aluminum hydride, and the mixture was refluxed for 3.5 hours. After cooling, a 10% ammonium chloride solution was added, while cooling was continued; then the mixture was suction-filtered, and the filtrate was concentrated by evaporation. The residue was purified on a silica gel column with methylene chloride. The fractions were concentrated by evaporation, the residue was dissolved in acetone, and the dihydrochloride was precipitated with methanolic hydrochloric acid.

Workup

  1. temperaturethe mixture was refluxed for 3.5 hours
  2. temperatureAfter cooling
  3. temperaturewhile cooling
  4. filtrationthen the mixture was suction-filtered
  5. concentrationthe filtrate was concentrated by evaporation
  6. customThe residue was purified on a silica gel column with methylene chloride
  7. concentrationThe fractions were concentrated by evaporation
  8. dissolutionthe residue was dissolved in acetone
  9. customthe dihydrochloride was precipitated with methanolic hydrochloric acid

Sources & evidence

ORD record
ord-b90c1f13b24b436e9c45f0af654b5e7f
Source dataset
uspto-grants-1984_12
Patent number
US04490369

Reaction notes

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