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 131425ノート

反応式

HRID 131425 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c2882176fd9a4785b63d8dd037b2ea89
出典データセット
uspto-grants-2008_06
特許番号
US07384934B2

反応ノート

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