Butylamine → N-butyl-1,1-dimethyl-1-sila-2-azacyclopentane

Reaction equation

[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].Cl[CH2:7][CH2:8][CH2:9][Si:10]([CH3:13])([CH3:12])Cl>>[CH2:1]([N:5]1[CH2:7][CH2:8][CH2:9][Si:10]1([CH3:13])[CH3:12])[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 8007Butylamine

HCID 82765Silane, chloro(3-chloropropyl)dimethyl-

Product 1

HCID 12863826N-butyl-1,1-dimethyl-1-sila-2-azacyclopentane

Conditions

Temperature: 10 °C

Procedure

An initial charge of 508 g (6.94 mol) of 1-butylamine is admixed dropwise over the course of 2.5 h with 171 g (1.00 mol) of chloropropyldimethylchlorosilane and the mixture is heated at reflux for 12 h. Following distillative removal of the excess 1-butylamine, the residue is diluted with 350 ml of toluene and cooled to 10° C. The precipitate it forms is filtered off and the filtrate is distilled in vacuo. This gives 134.5 g of N-butyl-1,1-dimethyl-1-sila-2-azacyclopentane.

Workup

temperaturethe mixture is heated
temperatureat reflux for 12 h
customremoval of the excess 1-butylamine
additionthe residue is diluted with 350 ml of toluene
filtrationThe precipitate it forms is filtered off
distillationthe filtrate is distilled in vacuo

Sources & evidence

ORD record: ord-cac1f95d9a934ec6b9bb2fa21fb32c46
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906179B2

Reaction notes

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