Ethanol → (+/-)cis-1-(2-Benzylphenoxy)-2-dimethylaminoindane Hydrochloride

HRID 965235Notes

Reaction equation

HRID 965235 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([C:14]1[CH:38]=[CH:37][CH:36]=[CH:35][C:15]=1[O:16][C@@H:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][C@@H:18]1[N:26]([CH3:34])[C:27](OC(C)(C)C)=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O1CCCC1.C(O)C.C(Cl)(Cl)[Cl:48]>>[ClH:48].[CH2:7]([C:14]1[CH:38]=[CH:37][CH:36]=[CH:35][C:15]=1[O:16][C@@H:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][C@@H:18]1[N:26]([CH3:34])[CH3:27])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 6212ChloroformHCID 8028TetrahydrofuranHCID 18661285cis-1-(2-benzylphenoxy)-2-(N-methyl-N-tert-butoxycarbonylamino)indaneHCID 21226445Aluminium lithium hydride

Product 1

HCID 18661281(+/-)cis-1-(2-Benzylphenoxy)-2-dimethylaminoindane Hydrochloride

Procedure

The title compound was prepared in a similar manner to Example 12 from LiAlH4 (401 mg, 10.6 mmol), cis-1-(2-benzylphenoxy)-2-(N-methyl-N-tert-butoxycarbonylamino)indane (453 mg, 1.06 mmol) and tetrahydrofuran (50 ml). After a reaction time of 3 h the reaction was worked up as previously described and subjected to column chromatography on silica gel eluting with 5% ethanol in chloroform to afford a pale green oil (331 mg) which was converted to the HCl salt and crystallised to afford the title compound as a white solid. m.p. 222°-225° C. (from methanol-diethyl ether).

Workup

  1. customAfter a reaction time of 3 h

Sources & evidence

ORD record
ord-a6ce6845aa2148e28758720e45e70ba9
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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