N,N-Dimethyl-1,3-propanediamine → Pr3Sn(CH2)3NH(CH2)3NMe2

HRID 27459

Reaction equation

HRID 27459 reaction equation
Br[CH2:2][CH2:3][CH2:4][Sn:5]([CH2:12][CH2:13][CH3:14])([CH2:9][CH2:10][CH3:11])[CH2:6][CH2:7][CH3:8].[CH3:15][N:16]([CH3:21])[CH2:17][CH2:18][CH2:19][NH2:20].C(=O)(O)[O-].[Na+]>C(OCC)C>[Sn:5]([CH2:4][CH2:3][CH2:2][NH:20][CH2:19][CH2:18][CH2:17][N:16]([CH3:21])[CH3:15])([CH2:12][CH2:13][CH3:14])([CH2:9][CH2:10][CH3:11])[CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 3314893-Bromopropyl(tripropyl)stannaneHCID 516892Sodium Bicarbonate

Product 1

HCID 131711878Pr3Sn(CH2)3NH(CH2)3NMe2Yield 77%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

Over a period of 0.5 hour 9.25 g (0.025 mol) of (3-bromopropyl) tripropyltin was added to 25 ml of 3-dimethylaminopropyl amine at room temperature. The mixture was stirred for 1 hour at 60° C. Under cooling 75 ml of diethylether and 60 ml of a 15% aqueous solution of sodium bicarbonate were added. After stirring for 0.5 hour the organic phase was separated, dried and evaporated in vacuo. Distillation gave 7.5 g (77%) of Pr3Sn(CH2)3NH(CH2)3NMe2 ; b.p. 113°-114° C./0.1 mm Hg, nD20 =1.4855.

Workup

  1. additionwere added
  2. stirringAfter stirring for 0.5 hour the organic phase
  3. customwas separated
  4. customdried
  5. customevaporated in vacuo
  6. distillationDistillation

Sources & evidence

ORD record
ord-134ee4dc025f410bb38c262b1f0f4ea8
Source dataset
uspto-grants-1980_09
Patent number
US04221811

Linked notes

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