Ethanol → (+/-)trans-1-(4-Benzyloxyphenoxy)-2-methylaminoindane Hydrochloride

HRID 965239Notes

Reaction equation

HRID 965239 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][C:15]1[CH:36]=[CH:35][C:18]([O:19][C@@H:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22][C@H:21]2[NH:29][C:30](OCC)=O)=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O1CCCC1.C(O)C.C(Cl)(Cl)[Cl:46]>>[ClH:46].[CH2:7]([O:14][C:15]1[CH:36]=[CH:35][C:18]([O:19][C@@H:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22][C@H:21]2[NH:29][CH3:30])=[CH:17][CH:16]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 6212ChloroformHCID 8028TetrahydrofuranHCID 18661303trans-1-(4-Benzyloxyphenoxy)-2-ethoxycarbonylaminoindaneHCID 21226445Aluminium lithium hydride

Product 1

HCID 18661304(+/-)trans-1-(4-Benzyloxyphenoxy)-2-methylaminoindane Hydrochloride

Procedure

The title compound was prepared in a similar manner to Example 12 from LiAlH4 (190 mg, 5 mmol), trans-1-(4-benzyloxyphenoxy)-2-ethoxycarbonylaminoindane (750 mg, 1.7 mmol) and tetrahydrofuran (50 ml). After a reaction time of 18 h at room temperature and a further hour at reflux, the reaction was worked up as previously described and subjected to column chromatography on silica gel eluting with 2% ethanol in chloroform to afford a pale yellow oil (290 mg) which was converted to the HCl salt and crystallised to afford the title compound as a white solid. m.p. 185°-187° C. (from methanol-diethyl ether).

Sources & evidence

ORD record
ord-1c83e25b7281407fa0be11e501883385
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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