Hydrochloric Acid → HCID 20353235, compound

HRID 372093Notes

Reaction equation

HRID 372093 reaction equation
[CH2:1]([N:8]1[CH2:12][C:11]23[CH2:22][CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[C:10]2=[CH:9]1)[C:14]1[CH:23]=[CH:24][CH:25]=[CH:26][C:13]3=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.C([BH3-])#N.[Na+].Cl>C(O)(=O)C>[CH2:1]([N:8]1[CH2:12][C:11]23[CH2:22][CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[CH:10]2[CH2:9]1)[C:14]1[CH:23]=[CH:24][CH:25]=[CH:26][C:13]3=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 70622570HCID 70622570, compound

Product 1

HCID 20353235HCID 20353235, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 37.7 g of finely powdered 2-benzyl-2,3-dihydro-8H-3a, 8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c] pyrrole (5e), 300 ml of methanol, and 40 ml of acetic acid is cooled with ice, and 14.8 g of sodium cyanoborohydride is added slowly with stirring. The mixture is stirred at room temperature for 3 hours, cooled, and treated with 50 ml of conc. hydrochloric acid. After stirring at room temperature for 0.5 hour the mixture is made basic and extracted several times with methylene chloride. Removal of the solvent from the dried extracts gives 37.5 g of 2-benzyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]-cyclohepta[1,2-c]pyrrole, identical by nmr spectroscopy with the product obtained in Example 4. The hydrochloride melts with decomposition at 195°-200° after crystallization from ethanol.

Workup

  1. additionis added slowly
  2. stirringThe mixture is stirred at room temperature for 3 hours
  3. temperaturecooled
  4. stirringAfter stirring at room temperature for 0.5 hour the mixture
  5. extractionextracted several times with methylene chloride
  6. customRemoval of the solvent from the dried extracts

Sources & evidence

ORD record
ord-64d947fdbe52434494a317dacd7911f0
Source dataset
uspto-grants-1978_05
Patent number
US04088772

Reaction notes

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