Thionyl Chloride → 1,2,3,6-Tetrahydro-4-phenylpyridine

HRID 255576Notes

Reaction equation

HRID 255576 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH:3]([C:14](O)=O)[CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O[CH2:24][CH:25]1[CH2:37][C:36]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[NH:29][C:28]=2[CH2:27][CH2:26]1.O=S(Cl)[Cl:40].P(Br)(Br)[Br:43]>C(#N)C>[Cl:40][CH2:14][CH:3]1[CH2:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:12][C:13]=2[CH2:1][CH2:2]1.[Br:43][CH2:24][CH:25]1[CH2:37][C:36]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[NH:29][C:28]=2[CH2:27][CH2:26]1.[C:6]1([C:5]2[CH2:4][CH2:3][NH:29][CH2:1][CH:13]=2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

9

Reactant 5

HCID 24386Thionyl ChlorideHCID 24614Phosphorus tribromideHCID 2823652,3,4,9-tetrahydro-1h-carbazol-3-ylmethanolHCID 13491214HCID 13491214, compoundHCID 21226445Aluminium lithium hydride

Product 3

HCID 825531,2,3,6-Tetrahydro-4-phenylpyridineHCID 13326801HCID 13326801, compoundHCID 134912153-(Bromomethyl)-2,3,4,9-tetrahydro-1H-carbazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2.19 g of 3-chloromethyl-1,2,3,4-tetrahydrocarbazole (or 2.63 g of 3-bromomethyl-1,2,3,4-tetrahydrocarbazole) (obtainable by reduction of 1,2,3,4-tetrahydrocarbazole-3-carboxylic acid with LiAlH4 to give 3-hydroxymethyl-1,2,3,4-tetrahydrocarbazole, followed by reaction with SOCl2 or PBr3) and 1.6 g of 4-phenyl-1,2,3,6-tetrahydropyridine in 10 ml of acetonitrile is stirred at 20° for 12 hours, worked up as usual and 3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)1,2,3,4-tetrahydrocarbazole ("P") is obtained. M.p. 163°-65°.

Sources & evidence

ORD record
ord-39483a14a89c45278cdd80c9de792ab1
Source dataset
uspto-grants-1987_10
Patent number
US04698351

Reaction notes

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