1,2-Dichloroethane → (S)-2-Isopropyl-11-[3-(2-methoxy-ethyl)-4-methyl-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine dihydrochloride

HRID 131425노트

반응식

HRID 131425 반응식
[CH:1]([C:4]1[CH:28]=[CH:27][C:7]2[NH:8][C:9]3[CH:26]=[CH:25][CH:24]=[CH:23][C:10]=3[N:11]=[C:12]([N:13]3[CH2:18][CH2:17][NH:16][C@@H:15]([CH2:19][CH2:20][O:21][CH3:22])[CH2:14]3)[C:6]=2[CH:5]=1)([CH3:3])[CH3:2].C=O.[C:31](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+].[Cl:50]CCCl>>[ClH:50].[ClH:50].[CH:1]([C:4]1[CH:28]=[CH:27][C:7]2[NH:8][C:9]3[CH:26]=[CH:25][CH:24]=[CH:23][C:10]=3[N:11]=[C:12]([N:13]3[CH2:18][CH2:17][N:16]([CH3:31])[C@@H:15]([CH2:19][CH2:20][O:21][CH3:22])[CH2:14]3)[C:6]=2[CH:5]=1)([CH3:3])[CH3:2]

참가 물질

6

반응물 5

HCID 111,2-DichloroethaneHCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 10249082(S)-2-Isopropyl-11-[3-(2-methoxy-ethyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine

생성물 1

HCID 69214411(S)-2-Isopropyl-11-[3-(2-methoxy-ethyl)-4-methyl-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine dihydrochloride

실험 절차

Combine (S)-2-isopropyl-11-[3-(2-methoxy-ethyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine (0.405 g, 1.07 mmol) and 37% formaldehyde solution (0.1 mL, 1.12 mmol) in 1,2-dichloroethane (25 mL). Stir for 10 minutes and add sodium triacetoxy borohydride (0.343 g, 1.60 mmol). Stir an additional 30 minutes and then pour solution onto saturated sodium bicarbonate solution. Extract with methylene chloride to give 0.489 g of the crude product. Silica gel chromatography, eluting with methylene chloride:methanol (100:10), gives 0.354 g of the title compound as the free base. The dihydrochloride salt precipitates in ethyl acetate as a solid: mp=210° C.; mass spectrum (ion spray): m/z=393 (M+1); Analysis for C24H34Cl2N4O: calcd: C, 61.93; H, 7.36; N, 12.04; found: C, 61.74; H, 7.47; N, 11.86.

후처리

  1. stirringStir an additional 30 minutes
  2. extractionExtract with methylene chloride
  3. customto give 0.489 g of the crude product
  4. washSilica gel chromatography, eluting with methylene chloride:methanol (100:10)

출처 및 근거

ORD 기록
ord-c2882176fd9a4785b63d8dd037b2ea89
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384934B2

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