Sodium hydride → (+/-) cis 2-Amino-1-(3,4dichlorophenoxy)indane Hydrochloride

HRID 965242Notes

Reaction equation

HRID 965242 reaction equation
[NH2:1][C@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1[OH:11].[H-].[Na+].[Cl:14][C:15]1[CH:20]=[CH:19][C:18](F)=[CH:17][C:16]=1[Cl:22]>>[ClH:14].[NH2:1][C@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1[O:11][C:18]1[CH:19]=[CH:20][C:15]([Cl:14])=[C:16]([Cl:22])[CH:17]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 740281,2-Dichloro-4-fluorobenzeneHCID 11205854(1R,2S)-2-amino-2,3-dihydro-1H-inden-1-ol

Product 1

HCID 86752858(+/-) cis 2-Amino-1-(3,4dichlorophenoxy)indane Hydrochloride

Procedure

The title compound was prepared in a similar manner to Example 26 from (±) cis 2-amino-1-indanol (2.24 g, 15.0 mmol), sodium hydride (0.54 g of an 80% dispersion in oil; 18.0 mmol) and 1,2-dichloro-4-fluorobenzene (2.97 g, 18.0 mmol). The crude product was purified by chromatography on silica eluting with 0-4% ethanol in diethyl ether. The resulting light brown oil (3.89 g) was extracted into a mixture of hexane and diethyl ether and treated with ethereal HCl to give the hydrochloride salt. Recrystallisation afforded the title compound as a colourless solid, m.p. 214°-215° C. (dec) (from methanol/ethyl acetate/diethyl ether).

Workup

  1. customThe crude product was purified by chromatography on silica eluting with 0-4% ethanol in diethyl ether
  2. extractionThe resulting light brown oil (3.89 g) was extracted into a mixture of hexane and diethyl ether
  3. additiontreated with ethereal HCl

Sources & evidence

ORD record
ord-e82fe50325f74afe8e09e121d8c1a2b8
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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