Acetonitrile → 2,2,6,6-Tetramethylpiperidine

HRID 2378153Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=C[C:5](N)=[CH:4][C:3]=1N.[C:10](#[N:12])[CH3:11].[CH2:13]1COCC1>>[CH3:11][C:10]1([CH3:13])[CH2:5][CH2:4][CH2:3][C:2]([CH3:7])([CH3:1])[NH:12]1

Participants

Reactant 3

HCID 6342Acetonitrile

HCID 72612,4-Diaminotoluene

HCID 8028Tetrahydrofuran

Product 1

HCID 130352,2,6,6-Tetramethylpiperidine

Procedure

Four amine bases were examined (Table 2) in THF or acetonitrile. Of the 4 amines examined, 2,2,6,6-tetramethylpiperidine gave the best results in both acetonitrile and THF (72%, 65%). Piperidine, which was used in the previous method, gave a low yield.

Sources & evidence

ORD record: ord-16ef94dd5bfe480382242608e42fca0c
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470785B2

Reaction notes

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