Hydrochloric Acid → N-Methyl-7-methyl-1,2,6,7-tetrahydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine-6-methanamine dihydrochloride

HRID 579983Notes

Reaction equation

HRID 579983 reaction equation
[CH:1]([N:3]1[CH:9]([CH2:10][NH:11][CH:12]=O)[C:8]2[CH:14]=[CH:15][CH:16]=[C:17]3[CH2:18][CH2:19][N:6]([C:7]=23)[C:5]2[CH:20]=[CH:21][CH:22]=[CH:23][C:4]1=2)=O.[ClH:24]>O1CCCC1.CO>[ClH:24].[ClH:24].[CH3:12][NH:11][CH2:10][CH:9]1[C:8]2[CH:14]=[CH:15][CH:16]=[C:17]3[CH2:18][CH2:19][N:6]([C:7]=23)[C:5]2[CH:20]=[CH:21][CH:22]=[CH:23][C:4]=2[N:3]1[CH3:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 14156737N-[7-formyl-1,2,6,7-tetrahydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-ylmethyl]-formamide

Product 1

HCID 14156739N-Methyl-7-methyl-1,2,6,7-tetrahydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine-6-methanamine dihydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of N-[7-formyl-1,2,6,7-tetrahydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-ylmethyl]-formamide (8.27 g) in tetrahydrofuran (220 ml) was added borane-dimethylsulfide complex in tetrahydrofuran (2M, 67 ml) at room temperature under nitrogen over a period of 30 minutes. The mixture was stirred at room temperature for 2 hours and thereafter refluxed for 30 minutes. The mixture was cooled to room temperature and treated slowly with methanol to destroy the excess borane. The solvent was removed with a rotary evaporator to afford an oil. This was dissolved in methanol (25 ml) and concentrated hydrochloric acid (8 ml), and the mixture was refluxed for 30 minutes. The mixture was concentrated on a rotary evaporator to dryness (55° C., high vacuum) to afford an oil. The oil was crystallized from a mixture of methanol (small amount) and ether (200 ml) to give 9.27 g of crystals. This solid was recrystallized from hot methanol (25 ml) to give 6.37 g of crystals, m.p. 194°-196.5° C.

Workup

  1. temperaturerefluxed for 30 minutes
  2. temperatureThe mixture was cooled to room temperature
  3. customto destroy the excess borane
  4. customThe solvent was removed with a rotary evaporator
  5. customto afford an oil
  6. concentrationThe mixture was concentrated on a rotary evaporator to dryness (55° C., high vacuum)
  7. customto afford an oil
  8. customThe oil was crystallized from a mixture of methanol (small amount) and ether (200 ml)

Sources & evidence

ORD record
ord-5c58687cf8404deea07628a071ca2bd5
Source dataset
uspto-grants-1988_06
Patent number
US04751223

Reaction notes

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