6,7-dihydro-5H-dibenzo[a,c]-cyclohepten-4-carboxamide → 6,7-dihydro-5H-dibenzo[a,c]cyclohepten-4-methanamine

HRID 1982621Notes

Reaction equation

HRID 1982621 reaction equation
[CH:1]1[C:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][CH2:10][CH2:11][C:5]=2[C:4]([C:16]([NH2:18])=O)=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH:1]1[C:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][CH2:10][CH2:11][C:5]=2[C:4]([CH2:16][NH2:18])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 133912786,7-dihydro-5H-dibenzo[a,c]-cyclohepten-4-carboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 133912796,7-dihydro-5H-dibenzo[a,c]cyclohepten-4-methanamineYield 14.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a dry nitrogen atmosphere 6,7-dihydro5H-dibenzo[a,c]-cyclohepten-4-carboxamide (0.78 gram, 0.0033 mole) was reacted with lithium aluminum hydride (0.2 gram, 0.0053 mole) in tetrahydrofuran (100 ml) to produce a white solid. The solid was recrystallized from a solution of diethyl ether and petroleum ether to provide 6,7-dihydro-5H-dibenzo[a,c]cyclohepten-4-methanamine (0.11 g, mp 200°-210°). The solvent was removed from the mother liquor to yield an additional 0.5 gram of the amine.

Workup

  1. customto produce a white solid
  2. customThe solid was recrystallized from a solution of diethyl ether and petroleum ether

Sources & evidence

ORD record
ord-ce91caf968c04c6a90c392db65e888ee
Source dataset
uspto-grants-1986_06
Patent number
US04596892

Reaction notes

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