Ammonium Chloride → HCID 13319961, compound

HRID 1154687Notes

Reaction equation

HRID 1154687 reaction equation
[CH3:1][O:2][C:3]1[C:32]([O:33][CH3:34])=[CH:31][C:6]2[C:7](=[O:30])[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-:41].[NH4+]>CCOCC.O1CCCC1.CC(C)=O>[ClH:41].[ClH:41].[OH:30][CH:7]1[C:6]2[CH:31]=[C:32]([O:33][CH3:34])[C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][N:15]([CH3:28])[CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)[CH2:8]1

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 20433677HCID 20433677, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13319961HCID 13319961, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.45 gm (5 mmols) of 1-[7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-1,2-dion-3-yl]-3-[N-methyl-N-(2-{3,4-dimethoxy-phenyl}-ethyl)-amino]-propane were dissolved in a mixture of 100 ml of ether and 50 ml of tetrahydrofuran, and then 0.76 gm of lithium aluminum hydride were added in batches, while stirring. The resulting mixture was refluxed for one hour, cooled with ice water and mixed with 15% ammonium chloride solution. The hydroxide precipitate was suction-filtered off and washed with ether, and the filtrate was concentrated by evaporation. After the free base product thus obtained had been dissolved in acetone, the dihydrochloride was precipitated with methanolic hydrochloric acid.

Workup

  1. temperatureThe resulting mixture was refluxed for one hour
  2. filtrationThe hydroxide precipitate was suction-filtered off
  3. washwashed with ether
  4. concentrationthe filtrate was concentrated by evaporation
  5. customAfter the free base product thus obtained
  6. customthe dihydrochloride was precipitated with methanolic hydrochloric acid

Sources & evidence

ORD record
ord-f40a695af7de4e0bb3421d6deed6aff0
Source dataset
uspto-grants-1984_12
Patent number
US04490369

Reaction notes

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