Lithium amide → 1,1-Dimethyl-5-(3-phenylpropoxy)-2-pentynamine

HRID 483473

Reaction equation

HRID 483473 reaction equation
[CH3:1][C:2]([NH2:6])([C:4]#[CH:5])[CH3:3].[Li+].[NH2-].Br[CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>N>[CH3:1][C:2]([CH3:3])([NH2:6])[C:4]#[C:5][CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 24532Lithium amideHCID 763193-Butyn-2-amine, 2-methyl-HCID 19797996(3-(2-Bromoethoxy)propyl)benzene

Product 1

HCID 137472431,1-Dimethyl-5-(3-phenylpropoxy)-2-pentynamineYield 13.8%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent2×

Procedure

1,1-Dimethylpropargylamine (8.5 g) was added dropwise to a suspension of lithamide [from lithium (1.7 g)] in liquid ammonia (100 ml) at -33°. The mixture was stirred for 90 min and a solution of [3-(2-bromoethoxy)propyl]benzene (21.5 g) in ER (30 ml) was added dropwise. The suspension was stirred for 4 h and ammonia was allowed to evaporate overnight. The residue was treated with H2O (100 ml) and extracted with ER (3×100 ml). The dried extract was evaporated and the residue was distilled to give the title compound as a colourless oil (3.0 g) b.p. 160°-165°/0.2 mmHg. T.l.c. (ER) Rf 0.3.

Workup

  1. stirringThe suspension was stirred for 4 h
  2. customto evaporate overnight
  3. additionThe residue was treated with H2O (100 ml)
  4. extractionextracted with ER (3×100 ml)
  5. extractionThe dried extract
  6. customwas evaporated
  7. distillationthe residue was distilled

Sources & evidence

ORD record
ord-64516877e9db4c6691c089b0b9851cfa
Source dataset
uspto-grants-1993_07
Patent number
US05225445

Linked notes

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