Water → HCID 67248432, compound

HRID 2175095Notes

Reaction equation

HRID 2175095 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]2[N:18]=[C:17]([C:19]3[CH:28]=[C:27]4[C:22]([C:23]([CH3:31])([CH3:30])[CH2:24][CH2:25][C:26]4=[O:29])=[CH:21][CH:20]=3)[CH:16]=[CH:15][CH:14]=2)[CH2:9][CH2:8]1.C[Li].O.[C:35](=O)([O-])O.[Na+]>C1COCC1.C(OCC)C>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([C:13]2[N:18]=[C:17]([C:19]3[CH:28]=[C:27]4[C:22]([C:23]([CH3:31])([CH3:30])[CH2:24][CH2:25][C:26]4([CH3:35])[OH:29])=[CH:21][CH:20]=3)[CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:12]1

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 53251220HCID 53251220, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 67248432HCID 67248432, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

50 mg (0.12 mmol) of 7-{6-[4-(5-hydroxypentyl)piperazin-1-yl]pyridin-2-yl}-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one are dissolved in 5 ml of THF, cooled to 0° C., and 224 μl (0.36 mmol) of methyllithium in diethyl ether (5%) are added. The reaction mixture is stirred at 0° C. for 30 min and warmed to room temperature. Water added to the reaction mixture, sodium hydrogencarbonate solution added, and the mixture extracted with ethyl acetate, dried and evaporated. The crude product is purified by means of column chromatography on silica gel.

Workup

  1. temperaturewarmed to room temperature
  2. additionadded
  3. extractionthe mixture extracted with ethyl acetate
  4. customdried
  5. customevaporated
  6. customThe crude product is purified by means of column chromatography on silica gel

Sources & evidence

ORD record
ord-ec26531a1b3147a49f9bc954530a2c82
Source dataset
uspto-grants-2015_06
Patent number
US09062015B2

Reaction notes

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