Aluminium lithium hydride → (+/-) trans 1-(3,4-Dichlorophenylthio)-2-methylaminoindane Hydrochloride

HRID 965232Notes

Reaction equation

HRID 965232 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:9]=[C:10]([S:15][C@@H:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][C@H:17]2[NH:25][C:26](OCC)=O)[CH:11]=[CH:12][C:13]=1[Cl:14]>C(OCC)C>[ClH:7].[Cl:7][C:8]1[CH:9]=[C:10]([S:15][C@@H:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][C@H:17]2[NH:25][CH3:26])[CH:11]=[CH:12][C:13]=1[Cl:14]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 53664910(+/-) trans 1-(3,4-Dichlorophenylthio)-2-ethoxycarbonylaminoindane

Product 1

HCID 86752857(+/-) trans 1-(3,4-Dichlorophenylthio)-2-methylaminoindane Hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of LiAlH4 (0.34 g, 9.05 mmol) in dry diethyl ether under nitrogen was added a solution of (±) trans 1-(3,4-dichlorophenylthio)-2-ethoxycarbonylaminoindane (0.69 g, 1.81 mmol) in diethyl ether. After stirring at room temperature overnight, the reaction was worked up as described for Example 2, and then purified on a silica gel column using 1% ethanol in chloroform as eluant. The resulting oil (0.26 g) was extracted into n-pentane and treated with ethereal hydrogen chloride to give the title compound as a colourless solid, m.p. 143°-144° C. (from methanol/diethyl ether).

Workup

  1. custompurified on a silica gel column
  2. extractionThe resulting oil (0.26 g) was extracted into n-pentane
  3. additiontreated with ethereal hydrogen chloride

Sources & evidence

ORD record
ord-a53d191abf1c49e3afe739de28ecb880
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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