Dimethylamine → N,N-Dimethyl-3-(tributylstannyl)propan-1-amine

HRID 27458Notes

Reaction equation

HRID 27458 reaction equation
[Sn:1]([CH2:14][CH2:15][CH2:16]Br)([CH2:10][CH2:11][CH2:12][CH3:13])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH2:4][CH3:5].[NH:18]([CH3:20])[CH3:19]>>[CH3:19][N:18]([CH3:20])[CH2:16][CH2:15][CH2:14][Sn:1]([CH2:10][CH2:11][CH2:12][CH3:13])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 23343000(3-Bromopropyl)(tributyl)stannane

Product 1

HCID 325472N,N-Dimethyl-3-(tributylstannyl)propan-1-amineYield 86%

Procedure

In a reaction vessel provided with a carbon dioxide condenser, a mixture of 6.18 g (0.015 mol) of Bu3Sn(CH2)3Br and 20 ml of Me2NH was refluxed for 7 h. The residue obtained after evaporation of the excess of Me2NH was taken up in 30 ml of diethyl ether and treated for 15 min with 50 ml of a 10% aqueous solution of NaHCO3. Distillation gave 4.95 g (86%) of (3-dimethylaminopropyl)tributyltin.

Workup

  1. customIn a reaction vessel provided with a carbon dioxide condenser
  2. temperaturewas refluxed for 7 h
  3. customThe residue obtained
  4. customafter evaporation of the excess of Me2NH
  5. additiontreated for 15 min with 50 ml of a 10% aqueous solution of NaHCO3
  6. distillationDistillation

Sources & evidence

ORD record
ord-d2badf8a65af43c98ff0e47b99da0e01
Source dataset
uspto-grants-1980_09
Patent number
US04221811

Reaction notes

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