Water → HCID 11652324, compound

HRID 2060061Notes

Reaction equation

HRID 2060061 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[CH3:13][N:14]([CH2:16][CH:17]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:26][CH3:27])[CH:23]=2)[C:18]1=[O:28])[CH3:15].O>C(OCC)C>[CH3:15][N:14]([CH2:16][CH:17]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:26][CH3:27])[CH:23]=2)[C:18]1([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[OH:28])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 122863-BromopyridineHCID 68804702HCID 68804702, compoundHCID 178418339Butyllithium

Product 1

HCID 11652324HCID 11652324, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

47 ml of n-butyllithium solution (1.6 mol./l in n-hexane) were added dropwise at a temperature of from −30 to −35° C. to a solution of 7.3 ml of 3-bromopyridine in about 125 ml of diethyl ether p.a. After a further 20 minutes at that temperature, 11 g of 2-dimethylaminomethyl-5-methoxy-indan-1-one, dissolved in diethyl ether p.a., were added dropwise, with continued cooling, stirring was continued for 40 minutes at that temperature, and heating was carried out overnight to room temperature. Then 46 ml of water were added at from −10 to 0° C., the phases were separated, the aqueous phase was extracted with diethyl ether (monitoring by thin-layer chromatography), and the combined organic phases were washed with saturated sodium chloride solution and dried over magnesium sulfate, filtered and concentrated. The resulting crude product was chromatographed on silica gel with ethyl acetate/25% ammonia solution (v/v=98:2). 7.06 g of 2-dimethylaminomethyl-5-methoxy-1-pyridin-3-yl-indan-1-ol were obtained and were dissolved in about 125 ml of 2-butanone p.a. and converted into the corresponding hydrochloride with about 0.3 ml of water and about 4.2 ml of chlorotrimethylsilane, while cooling with ice; the hydrochloride was filtered off with suction with the exclusion of air and dried in vacuo (about 50 mbar) (yield 6.79 g, mixture of the two diastereoisomers).

Workup

  1. addition, were added dropwise, with continued cooling
  2. temperatureheating
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted with diethyl ether (monitoring by thin-layer chromatography)
  5. washthe combined organic phases were washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting crude product was chromatographed on silica gel with ethyl acetate/25% ammonia solution (v/v=98:2)

Sources & evidence

ORD record
ord-9044020478ce4209bdf057b1fdb2887a
Source dataset
uspto-grants-2012_10
Patent number
US08278338B2

Reaction notes

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