2-Mercaptoethanol → 1,2,3,6-Tetrahydro-4-phenylpyridine

HRID 2290579Notes

Reaction equation

HRID 2290579 reaction equation
CN([CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2N[CH:6]=1)C.SCCO.O[CH2:19][CH2:20][S:21][CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1.O=S(Cl)[Cl:34].P(Br)(Br)[Br:37]>C(#N)C>[Cl:34][CH2:19][CH2:20][S:21][CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1.[Br:37][CH2:19][CH2:20][S:21][CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1.[C:9]1([C:5]2[CH2:4][CH2:24][NH:25][CH2:26][CH:6]=2)[CH:8]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

9

Reactant 5

HCID 15672-MercaptoethanolHCID 6890GramineHCID 24386Thionyl ChlorideHCID 24614Phosphorus tribromideHCID 12272369Ethanol, 2-[(1H-indol-3-ylmethyl)thio]-

Product 3

HCID 825531,2,3,6-Tetrahydro-4-phenylpyridineHCID 13314328HCID 13314328, compoundHCID 20231223HCID 20231223, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2.26 g of 3-(4-chloro-2-thiabutyl)indole [or 2.70 g of 3-(4-bromo-2-thiabutyl)indole which may be obtained by reaction of gramine with 2-mercaptoethanol to give 3-(4-hydroxy-2-thiabutyl)indole and subsequent 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° C. for 12 hours, worked up as usual and 3-[4-(4-phenyl-1,2,3,6-tetrahydropyridyl)-2-thiabutyl]indole ("P") of m.p. 109° is obtained.

Sources & evidence

ORD record
ord-39ab19a8e0fe482ab58786d25b174da3
Source dataset
uspto-grants-1986_10
Patent number
US04617309

Reaction notes

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