Ammonia → HCID 21519708, compound

HRID 1283296Notes

Reaction equation

HRID 1283296 reaction equation
[CH:1]12[C:13](=O)[CH:5]3[C:6]4[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=4[CH:8]1[CH:2]2[C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=13.[BH4-].[Na+].[NH3:21]>CO>[CH:1]12[CH:13]([NH2:21])[CH:5]3[C:6]4[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=4[CH:8]1[CH:2]2[C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=13

Participants

5

Reactant 3

HCID 222AmmoniaHCID 4311764Sodium borohydrideHCID 12117541HCID 12117541, compound

Product 1

HCID 21519708HCID 21519708, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An amount of 464 mb (2mMoles) of 1,1a,6,10b-tetrahydro-1,6-methano-dibenzo[a,e]cyclopropa[c]cyclohepten-11-one is dissolved in 15 ml of a 15% solution of ammonia in methanol, and the solution allowed to stand in a closed flask for 48 hours at 20°. An addition is then made at ca. 20°, with stirring, of 152 mg of sodium borohydride. After 30 minutes, the reaction mixture is briefly refluxed and again cooled. Processing is carried out analogously to Example 1 to obtain 1,1a,6,10b-tetrahydro-1,6-methano-dibenzo[a,e]cyclopropa[c]cycloheptene-11-amine; M.P. 126°-127°.

Workup

  1. additionAn addition
  2. customis then made at ca. 20°
  3. waitAfter 30 minutes
  4. temperaturethe reaction mixture is briefly refluxed
  5. temperatureagain cooled

Sources & evidence

ORD record
ord-cc16ac6b0dfd4d0194f2f85da776bd19
Source dataset
uspto-grants-1976_08
Patent number
US03974284

Reaction notes

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