Dichloromethane → 4-(1,2,3,6-tetrahydropyridin-4-yl)benzonitrile TFA

HRID 522854Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].C(Cl)Cl.[C:25]([OH:31])([C:27]([F:30])([F:29])[F:28])=[O:26]>>[NH:12]1[CH2:11][CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:14][CH2:13]1.[C:25]([OH:31])([C:27]([F:30])([F:29])[F:28])=[O:26]

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 11289112Tert-butyl 4-(4-cyanophenyl)-3,6-dihydropyridine-1(2h)-carboxylate

Product 1

HCID 866852394-(1,2,3,6-tetrahydropyridin-4-yl)benzonitrile TFAYield 87.6%

Procedure

To a solution of tert-butyl 4-(4-cyanophenyl)-5,6-dihydropyridine-1(2H)-carboxylate (332 mg, 1168 μmol) in CH2Cl2 (4.00 mL, 62167 μmol) was added TFA (0.0900 mL, 1168 μmol). The yellow solution was stirred at RT for 3 h. The reaction mixture was dried under reduced pressure providing an off-white crystalline material 4-(1,2,3,6-tetrahydropyridin-4-yl)benzonitrile-TFA (305 mg, 87.6%). MS (ESI, pos. ion) m/z: 185.4 (M+1).

Workup

customThe reaction mixture was dried under reduced pressure

Sources & evidence

ORD record: ord-d6fb3e8ad95545848de05770d39ae551
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334269B2

Reaction notes

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