Trifluoroacetic acid → 3-Amino-5-(3-ethoxypropyl)-5H-dibenzo[a,d]cycloheptene

HRID 225048Notes

Reaction equation

HRID 225048 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[C:7]([CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH3:22])(O)[C:6]=2[CH:23]=1.[BH4-].[Na+].FC(F)(F)C(O)=O>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH:7]([CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH3:22])[C:6]=2[CH:23]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 233288763-Amino-5-(3-ethoxypropyl)-5H-dibenzo[a,d]cyclohepten-5-ol

Product 1

HCID 123351493-Amino-5-(3-ethoxypropyl)-5H-dibenzo[a,d]cycloheptene

Procedure

3-Amino-5-(3-ethoxypropyl)-5H-dibenzo[a,d]cyclohepten-5-ol (10 g., 0.032 mole) and sodium borohydride (12.3 g., 0.325 mole) are ground together in a mortar. The mixture is added in portions to 250 ml. of trifluoroacetic acid, cooled in ice, and stirred vigorously under a stream of nitrogen in an efficient fume hood. Upon completion of the addition, the mixture is stirred for 15 minutes and the bulk of the trifluoroacetic acid removed under vacuum.

Workup

  1. additionThe mixture is added in portions to 250 ml
  2. additionUpon completion of the addition
  3. stirringthe mixture is stirred for 15 minutes
  4. customthe bulk of the trifluoroacetic acid removed under vacuum

Sources & evidence

ORD record
ord-31acb281c19242dd8919b06beaeef67f
Source dataset
uspto-grants-1980_11
Patent number
US04235820

Reaction notes

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