Hydrochloric Acid → 5,6-Dihydro-N,N-dimethyl-6-phenyl-11H-pyrido[2,3-b][1,4]benzodiazepine-11-propanamine, dihydrochloride hemihydrate

HRID 637465

Reaction equation

HRID 637465 reaction equation
[CH3:1][N:2]([CH3:27])[CH2:3][CH2:4][CH2:5][N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:9][C:8]2[CH:23]=[CH:24][CH:25]=[N:26][C:7]1=2.[ClH:28].[BH3-]C#N.[Na+].C[OH:34]>>[OH2:34].[ClH:28].[ClH:28].[CH3:27][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[NH:9][C:8]2[CH:23]=[CH:24][CH:25]=[N:26][C:7]1=2.[CH3:27][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[NH:9][C:8]2[CH:23]=[CH:24][CH:25]=[N:26][C:7]1=2.[ClH:28].[ClH:28]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 54961TampramineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 704878055,6-Dihydro-N,N-dimethyl-6-phenyl-11H-pyrido[2,3-b][1,4]benzodiazepine-11-propanamine, dihydrochloride hemihydrate

Procedure

A solution of 3.0 g (0.0064 mole) of N,N-dimethyl-6-phenyl-11H-pyrido[2,3-b][1,4]benzodiazepine-11-propanamine in absolute methanol was adjusted to pH 5.6 with methanolic hydrogen chloride solution. To this solution was added at one time, 0.7 g (0.011 mole) of NaBH3CN and the reaction mixture was refluxed for 20 min. The ethanol was removed in vacuo and the residue was partitioned between dilute sodium hydroxide and methylene chloride. The methylene chloride layer was dried over magnesium sulfate and concentrated to leave a residue which was twice crystallized from 2-propanol and isopropyl ether. A yellow solid, 1.6 g (57%) was obtained which loses its crystalline structure on heating starting at 156°-160° C. with decomposition at 180°-195° C.

Workup

  1. temperaturethe reaction mixture was refluxed for 20 min
  2. customThe ethanol was removed in vacuo
  3. customthe residue was partitioned between dilute sodium hydroxide and methylene chloride
  4. dry with materialThe methylene chloride layer was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customto leave a residue which
  7. customwas twice crystallized from 2-propanol and isopropyl ether
  8. customA yellow solid, 1.6 g (57%) was obtained which
  9. temperatureon heating
  10. customstarting at 156°-160° C. with decomposition at 180°-195° C.

Sources & evidence

ORD record
ord-84b33cd0652a48da9c04520fa3d12ec0
Source dataset
uspto-grants-1985_12
Patent number
US04556667

Linked notes

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