Hydrochloric Acid → HCID 13455624, compound

HRID 1032510Notes

Reaction equation

HRID 1032510 reaction equation
[CH2:1]([N:4]([CH2:23][CH2:24][CH3:25])[C:5](=O)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:9]([NH2:21])[CH:8]=1)[CH2:2][CH3:3].B.[ClH:27].O>O1CCCC1>[ClH:27].[ClH:27].[CH2:14]([O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][N:4]([CH2:1][CH2:2][CH3:3])[CH2:23][CH2:24][CH3:25])=[CH:8][C:9]=1[NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6331BoraneHCID 136292992-(3-Amino-4-benzyloxyphenyl)acetic acid dipropylamide

Product 1

HCID 13455624HCID 13455624, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 13.9 g of 2-(3-amino-4-benzyloxyphenyl)acetic acid dipropylamide in 65 ml of tetrahydrofuran is added dropwise under a nitrogen atmosphere into 12 ml of a one-molar solution of borane in tetrahydrofuran, cooled to +5° C., during a period of 20 minutes. Subsequently, the mixture is agitated for 4 hours at room temperature and refluxed for 22 hours. The mixture is combined with semiconcentrated hydrochloric acid and water and the tetrahydrofuran is distilled off. The aqueous solution is then adjusted to a pH value of 10 with sodium hydroxide and extracted by shaking with ether. The ether solution yields, after evaporation and chromatography on silica gel with methylene chloride/acetone (1:1), 8.93 g of pure 2-benzyloxy-5-(2-dipropylaminoethyl)-aniline as an oil. Treatment of this product with 2N HCl in methanol and evaporation yield 2-benzyloxy-5-(2-dipropylaminoethyl)aniline, dihydrochloride, mp 111°-112° C.

Workup

  1. temperaturecooled to +5° C., during a period of 20 minutes
  2. temperaturerefluxed for 22 hours
  3. distillationthe tetrahydrofuran is distilled off
  4. extractionextracted
  5. stirringby shaking with ether
  6. customThe ether solution yields
  7. customafter evaporation and chromatography on silica gel with methylene chloride/acetone (1:1), 8.93 g of pure 2-benzyloxy-5-(2-dipropylaminoethyl)-aniline as an oil
  8. customTreatment of this product with 2N HCl in methanol and evaporation

Sources & evidence

ORD record
ord-0c3b4cb8fbb34904b8702341f04874d5
Source dataset
uspto-grants-1990_09
Patent number
US04958026

Reaction notes

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