Phenethyl bromide → 1-(2-Phenylethyl)-3-(1-methyl-4-piperidinyl)-1H-indazole hydrobromide

HRID 986116Notes

Reaction equation

HRID 986116 reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][N:11]=2)[CH2:6][CH2:5]1.[Br:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Br.CCOCC>CN(C)C=O.CCOCC.O>[BrH:19].[C:22]1([CH2:21][CH2:20][N:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]([CH:7]3[CH2:6][CH2:5][N:4]([CH3:3])[CH2:9][CH2:8]3)=[N:11]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 7666Phenethyl bromideHCID 24758Sodium hydrideHCID 86739792Ether hydrobromideHCID 178480237HCID 178480237, compound

Product 1

HCID 140325111-(2-Phenylethyl)-3-(1-methyl-4-piperidinyl)-1H-indazole hydrobromideYield 36%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent3×

Procedure

To a stirred mixture of 0.86 g of sodium hydride (50% oil dispersion) in 50 ml of dimethylformamide was added, dropwise, 3.0 g of 3-(1-methyl-4-piperidinyl)-1H-indazole in 15 ml of hot dimethylformamide. The reaction mixture was stirred at ambient temperature for 1 hr and then a solution of 3.33 g of (2-bromoethyl)benzene in 10 ml of dimethylformamide was added dropwise. The reaction mixture was stirred for 21/2 days at ambient temperature, cooled to 0°, and water was added dropwise. The mixture was extracted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate and the solvent was removed in vacuo to yield an oil. The oil was dissolved in ether and a saturated hydrogen bromide/ether solution was added dropwise. The resultant solid was recrystallized two times from ethanol to yield 2.0 g (36%) of product, mp 163°-164° C.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred for 21/2 days at ambient temperature
  3. temperaturecooled to 0°
  4. extractionThe mixture was extracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed in vacuo
  8. customto yield an oil
  9. customThe resultant solid was recrystallized two times from ethanol

Sources & evidence

ORD record
ord-e07b1659e7c046da94f5766c36379bad
Source dataset
uspto-grants-1987_12
Patent number
US04710573

Reaction notes

Loading…