Sodium hydride → 1-Cyclopropylmethyl-3-(1-methyl-4-piperidinyl)-1H-indazole hydrobromide

HRID 652135

반응식

HRID 652135 반응식
[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.Cl[CH2:20][CH:21]1[CH2:23][CH2:22]1.[BrH:24].CCOCC>CN(C)C=O.CCOCC>[BrH:24].[CH:21]1([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)[CH2:23][CH2:22]1

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 80013(Chloromethyl)cyclopropaneHCID 86739792Ether hydrobromideHCID 178480237HCID 178480237, 화합물

생성물 1

HCID 140325091-Cyclopropylmethyl-3-(1-methyl-4-piperidinyl)-1H-indazole hydrobromide수율 32%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매3회

실험 절차

To a stirred mixture of 1.19 g of sodium hydride (50% oil dispersion) in 65 ml of dimethylformamide was added, dropwise, 4.0 g of 3-(1-methyl-4-piperidinyl)-1H-indazole in 20 ml of hot dimethylformamide. The mixture was stirred for 1 hr at ambient temperature and then 1.40 g of chloromethylcyclopropane in 10 ml of dimethylformamide was added dropwise. The reaction mixture was stirred for 21/2 days at ambient temperature. The reaction mixture was quenched with water, 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 saturated hydrogen bromide/ether solution was added dropwise to precipitate a salt. The salt was recrystallized from toluene and ethyl acetate to yield 2.8 g (32%) of product, mp 177°-179° C.

후처리

  1. additionwas added
  2. stirringThe reaction mixture was stirred for 21/2 days at ambient temperature
  3. customThe reaction mixture was quenched with water
  4. extractionextracted 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. customto precipitate a salt
  10. customThe salt was recrystallized from toluene and ethyl acetate

출처 및 근거

ORD 기록
ord-e0f9a700d0ef43138969234d00ec0ad2
출처 데이터셋
uspto-grants-1987_06
특허 번호
US04670447

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