Diethyl Ether → HCID 18950034, compound

HRID 1492957Notes

Reaction equation

HRID 1492957 reaction equation
I[CH2:2][CH2:3][CH3:4].[ClH:5].[NH2:6][CH:7]1[CH2:16][CH2:15][C:14]2[C:9](=[C:10]([O:18][CH3:19])[CH:11]=[CH:12][C:13]=2[F:17])[CH2:8]1.[C:20](=O)([O-])[O-].[K+].[K+].C(O[CH2:29][CH3:30])C>CC#N>[ClH:5].[F:17][C:13]1[CH:12]=[CH:11][C:10]([O:18][CH3:19])=[C:9]2[C:14]=1[CH2:15][CH2:16][CH:7]([N:6]([CH2:20][CH2:29][CH3:30])[CH2:2][CH2:3][CH3:4])[CH2:8]2

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 336431-Iodopropane2×HCID 18950036HCID 18950036, compound

Product 1

HCID 18950034HCID 18950034, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-iodopropane (0.89 ml) is added to a mixture of (+)-VII·HCl (1.01 g) and powdered potassium carbonate in 30 ml MeCN under nitrogen. The mixture is stirred at room temperature for 10 days during which two portions of 0.3 ml 1-iodopropane is added. After addition of diethyl ether, filtration and evaporation, the crude product purified by chromatography on alumina (diethyl ether/light petroleum, 1:4) to give 0.90 g of (+)-VIII·HCl and, on further elution, 0.23 g of (+)-5-fluoro-8-methoxy-2-propylaminotetralin hydrochloride, (+)-XI·HCl.

Workup

  1. additionis added
  2. customthe crude product purified by chromatography on alumina (diethyl ether/light petroleum, 1:4)

Sources & evidence

ORD record
ord-72940524f1074ac08ba484f1f8d39af5
Source dataset
uspto-grants-1994_12
Patent number
US05376687

Reaction notes

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