Ethanamine, 2,2,2-trifluoro- → Propranolol

HRID 1955757Notes

Reaction equation

HRID 1955757 reaction equation
F[C:2](F)(F)[CH2:3][NH:4][CH2:5][CH:6]([OH:19])[CH2:7][O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.F[C:23](F)(F)CN>>[CH3:2][CH:3]([NH:4][CH2:5][CH:6]([OH:19])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=12)[CH3:23]

Participants

3

Reactant 2

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 103799812-Propanol, 1-(1-naphthalenyloxy)-3-[(2,2,2-trifluoroethyl)amino]-

Product 1

HCID 4946PropranololYield 68%

Conditions

Temperature
100 °C

Procedure

(RS)-1-(2,2,2-TRIFLUOROETHYLAMINO)-3-(1-NAPHTHYLOXY)-2-PROPANOL ##STR2## A mixture of (2RS)-1'-(2,3-epoxypropoxy)naphthalene (1.4 g, 6.49 mmole) and 2,2,2,-trifluroethylamine (25 g, 252.4 mmole) were heated in a sealed glass tube for about 115 hours at 100° C., Excess amine was distilled under vacuum and collected. The remaining solid was dissolved in ether and washed twice with 250 ml of water. The ethereal solution was treated with dry hydrogen chloride gas to convert the amine to its hydrochloride salt which is collected as a off white solid ; m.p. 178°-180° C.; (yield 68%).

Workup

  1. distillationExcess amine was distilled under vacuum
  2. customcollected
  3. dissolutionThe remaining solid was dissolved in ether
  4. washwashed twice with 250 ml of water
  5. additionThe ethereal solution was treated with dry hydrogen chloride gas
  6. customis collected as a off white solid

Sources & evidence

ORD record
ord-2ca34168792743908942f38706373a33
Source dataset
uspto-grants-1998_07
Patent number
US05776985

Reaction notes

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