Sodium hydride → HCID 86752862, compound

HRID 965244Notes

Reaction equation

HRID 965244 reaction equation
[CH3:1][NH:2][C@H:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C@H:4]1[OH:12].[H-].[Na+].[Cl:15][C:16]1[CH:21]=[CH:20][C:19](F)=[CH:18][C:17]=1[Cl:23]>>[ClH:15].[Cl:15][C:16]1[CH:21]=[C:20]([CH:19]=[CH:18][C:17]=1[Cl:23])[O:12][C@@H:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:11][C@@H:3]1[NH:2][CH3:1]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 740281,2-Dichloro-4-fluorobenzeneHCID 69529496HCID 69529496, compound

Product 1

HCID 86752862HCID 86752862, compound

Procedure

The title compound was prepared in a similar manner to Example 26 from (±) cis 2-methylamino-1-indanol (0.815 g, 5.0 mmol), sodium hydride (0.18 g of an 80% dispersion in oil; 6.0 mmol) and 1,2-dichloro-4-fluorobenzene (0.99 g, 6.0 mmol). The crude product was purified by chromatography on silica eluting with 0-3% ethanol in diethyl ether. The resulting brown oil (1.3 g) was dissolved in hexane and treated with ethereal HCl to give the hydrochloride salt. Recrystallisation afforded the title compound as a colourless solid, m.p. 238°-239° C. (dec) (from methanoildiethyl ether).

Workup

  1. customThe crude product was purified by chromatography on silica eluting with 0-3% ethanol in diethyl ether
  2. dissolutionThe resulting brown oil (1.3 g) was dissolved in hexane
  3. additiontreated with ethereal HCl

Sources & evidence

ORD record
ord-cb7f490f26904dec924b7953e4160bc2
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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