Water → HCID 18477136, compound

HRID 2188201Notes

Reaction equation

HRID 2188201 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH2:10]([CH2:17][NH:18][CH2:19][CH:20]1[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([F:30])[CH:26]=2)[C:21]1=[O:31])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>C(OCC)C>[CH2:10]([CH2:17][NH:18][CH2:19][CH:20]1[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([F:30])[CH:26]=2)[C:21]1([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[OH:31])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 18477116HCID 18477116, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 18477136HCID 18477136, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Phenylmagnesium bromide (3 M solution in diethyl ether, 9 cm3) was added to dry diethyl ether (20 cm3) under nitrogen with stirring. This was then cooled to below 0° C. (salt-ice bath) and 2-(N-benzylmethylamino)methyl-6-fluoro-3,4-dihydro-2H-naphthalene-1-one hydrochloride was added in small portions at such a rate as to maintain the temperature below 0° C. (approx. 15 mins). The reaction mixture was stirred for a further 1 h at 0° C. and then poured onto ice. Water (100 cm3) and diethyl ether (100 cm3) were added and the aqueous layer was separated and extracted with further diethyl ether (100 cm3). The combined ether layers were extracted with hydrochloric acid (5 M, 3×50 cm3). The acidic extracts were basified (K2CO3) and re-extracted with dichloromethane (3×75 cm3). The combined extracts were dried (Na2SO4) and the solvent was removed under reduced pressure to provide the title compound (1.55 g) as a brown oil which solidified on standing.

Workup

  1. additionwas added in small portions at such a rate as
  2. temperatureto maintain the temperature below 0° C. (approx. 15 mins)
  3. stirringThe reaction mixture was stirred for a further 1 h at 0° C.
  4. additionpoured onto ice
  5. customthe aqueous layer was separated
  6. extractionextracted with further diethyl ether (100 cm3)
  7. extractionThe combined ether layers were extracted with hydrochloric acid (5 M, 3×50 cm3)
  8. extractionre-extracted with dichloromethane (3×75 cm3)
  9. dry with materialThe combined extracts were dried (Na2SO4)
  10. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fc12c25222cc478cbd74bb5f85beb85a
Source dataset
uspto-grants-2002_06
Patent number
US06410592B1

Reaction notes

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