Methylamine → 1-(Methylamino)cyclopentane-1-carbonitrile

HRID 2273907Notes

Reaction equation

[CH3:1][NH2:2].[C:3]1(=O)[CH2:7][CH2:6][CH2:5][CH2:4]1.C[Si]([C:13]#[N:14])(C)C>>[CH3:1][NH:2][C:3]1([C:13]#[N:14])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

Reactant 3

HCID 6329Methylamine

HCID 8452Cyclopentanone

HCID 82115Trimethylsilyl cyanide

Product 1

HCID 129454451-(Methylamino)cyclopentane-1-carbonitrile

Procedure

Methylamine was bubbled into a refrigerated mixture of cyclopentanone (0.252 g, 3 mmol) and trimethylsilyl cyanide (0.396 g, 4 mmol) until the volume doubled. The mixture was stirred 3 h and then concentrated to dryness to obtain 31a (0.372 g, quantitative).

Workup

concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-22432895973e4f95974cdcce64f57e8b
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126941B2

Reaction notes

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