Pyridine → 4-(4-Trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine-1-carbonylchloride

HRID 856051Notes

Reaction equation

Cl.[F:2][C:3]([F:17])([F:16])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH:15]=2)=[CH:6][CH:5]=1.N1C=CC=CC=1.[Cl:24][C:25](Cl)([O:27]C(=O)OC(Cl)(Cl)Cl)Cl>>[F:17][C:3]([F:2])([F:16])[C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH2:15][CH2:14][N:13]([C:25]([Cl:24])=[O:27])[CH2:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

Reactant 3

HCID 1049Pyridine

HCID 94429Triphosgene

HCID 215599794-[4-(Trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine--hydrogen chloride (1/1)

Product 1

HCID 230815564-(4-Trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine-1-carbonylchlorideYield 199.9%

Procedure

Using 4-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine hydrochloride (300 mg, 1.14 mmol) prepared in Reference Example 97, pyridine (0.18 ml, 2.28 mmol) and triphosgene (112 mg, 0.38 mmol), 4-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine-1-carbonylchloride (220 mg, yield 67%) as a yellow oil was prepared in the same manner as described in Reference Example 94.

Sources & evidence

ORD record: ord-2d9d68d454f5494b869d08b6969c1555
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262212B2

Reaction notes

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