Hydrochloric Acid → HCID 70486582, compound

HRID 1154674Notes

Reaction equation

HRID 1154674 reaction equation
[CH3:1][O:2][C:3]1[C:28]([O:29][CH3:30])=[CH:27][C:6]2[CH2:7][C:8](=[O:26])[N:9]([CH2:12][CH2:13][CH2:14][N:15]([CH3:25])[CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21](N)=[CH:20][CH:19]=3)[CH2:10][CH2:11][C:5]=2[CH:4]=1.N([O-])=O.[Na+].[ClH:35]>>[ClH:35].[ClH:35].[CH3:1][O:2][C:3]1[C:28]([O:29][CH3:30])=[CH:27][C:6]2[CH2:7][C:8](=[O:26])[N:9]([CH2:12][CH2:13][CH2:14][N:15]([CH3:25])[CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([Cl:35])=[CH:20][CH:19]=3)[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 20433767HCID 20433767, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 70486582HCID 70486582, compound

Conditions

Temperature
55 °C

Procedure

1.01 gm (0.00245 mol) of 1-[7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-methyl-N-(2{4-amino-phenyl}-ethyl)-amino]-propane were dissolved in 5 ml of semi-concentrated hydrochloric acid, and the solution was diazotized with 0.17 gm (0.00245 of sodium nitrite. Subsequently, the solution was stirred at 55° C. until no more nitrogen escaped. The solution was made weakly alkline and extracted with methylene chloride. After drying and evaporating in vacuo, the residueal oil was purified on aluminum oxide (200 gm, neutral, activity II; eluant: methylene chloride +2% of ethanol) and the dihydrochloride was precipitated from acetone with ethereal hydrochloric acid.

Workup

  1. extractionextracted with methylene chloride
  2. customAfter drying
  3. customevaporating in vacuo
  4. customthe residueal oil was purified on aluminum oxide (200 gm, neutral, activity II; eluant: methylene chloride +2% of ethanol)
  5. customthe dihydrochloride was precipitated from acetone with ethereal hydrochloric acid

Sources & evidence

ORD record
ord-cd1ce3e79b034b5187d2edb619b97b27
Source dataset
uspto-grants-1984_12
Patent number
US04490369

Reaction notes

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