2-Mercaptoethanol → HCID 19786784, compound

HRID 1657006Notes

Reaction equation

HRID 1657006 reaction equation
Cl[CH2:2][CH2:3][S:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[NH:8][CH:7]=1.BrCCSCC1C2C(=CC=C(C(OC)=[O:34])C=2)NC=1.SCCO>>[OH:34][CH2:2][CH2:3][S:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[NH:8][CH:7]=1

Participants

4

Reactant 3

HCID 15672-MercaptoethanolHCID 13520594HCID 13520594, compoundHCID 13520595HCID 13520595, compound

Product 1

HCID 19786784HCID 19786784, compound

Procedure

A solution of 28.4 g of methyl 3-(4-chloro-2-thiabutyl)-indole-5-carboxylate [or 32.8 g of methyl 3-(4-bromo-2-thiabutyl)-indole-5-carboxylate; obtainable by reacting methyl gramine-5-carboxylate with 2-mercaptoethanol to give methyl 3-(4-hydroxy-2-thiabutyl)-indole-5-carboxylate and subsequently reacting the latter with SOCl2 or PBr3 ] and 16 g of 4-phenyl-1,2,3,6-tetrahydropyridine in 100 ml of acetonitrile is stirred for 12 hours at 20° and is worked up in the customary manner to give methyl 3-[4-(4-phenyl-1,2,3,6-tetrahydropyridyl)-2-thiabutyl]-indole-5-carboxylate ("P"); hydrochloride, m.p. 202°-203°.

Sources & evidence

ORD record
ord-76e1ee86482c4822b2432f21e0b7a40f
Source dataset
uspto-grants-1993_10
Patent number
US05256673

Reaction notes

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