3,3,3-Triphenylpropan-1-ol → 2-(4-(3,3,3-Triphenylpropoxy)phenyl)ethylamine

HRID 363699Notes

Reaction equation

HRID 363699 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=O)(C)(C)C.[C:18]1([C:24]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:25][CH2:26]O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)(C)C>[C:18]1([C:24]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:25][CH2:26][O:17][C:14]2[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][NH2:8])=[CH:16][CH:15]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 2986573,3,3-Triphenylpropan-1-olHCID 11831452tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamate

Product 1

HCID 153897692-(4-(3,3,3-Triphenylpropoxy)phenyl)ethylamineYield 66%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

N-(t-butoxycarbonyl)-2-(4-hydroxyphenyl)ethylamine (1.3 g) and 3,3,3-triphenylpropanol (1.4 g) were coupled by the method of example 5. The product (1.4 g) was dissolved in 15 mL isopropanol containing 1.0 g HCl, and stirred 3 hr at room temperature. A precipitate formed, which was collected and recrystallized from ethanol-ether to provide the hydrochloride salt of the title compound as a white solid, mp 163°-165° C., in 66% yield. Anal. calcd. for C29H29NO·HCl·0.75 H2O: C, 76.13; H, 6.94; N, 3.06. Found: C, 75.99; H, 6.81; N, 3.02.

Workup

  1. customA precipitate formed
  2. customwhich was collected
  3. customrecrystallized from ethanol-ether

Sources & evidence

ORD record
ord-d8fa7503918b47a0b92f0f6fe052fe07
Source dataset
uspto-grants-1999_02
Patent number
US05874436

Reaction notes

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