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

HRID 131424ノート

反応式

HRID 131424 の反応式
[CH3:1][C:2]1[CH:26]=[CH:25][C:5]2[NH:6][C:7]3[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=3[N:9]=[C:10]([N:11]3[CH2:16][CH2:15][NH:14][C@@H:13]([CH2:17][CH2:18][O:19][CH3:20])[CH2:12]3)[C:4]=2[CH:3]=1.C=O.[C:29](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:1][C:2]1[CH:26]=[CH:25][C:5]2[NH:6][C:7]3[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=3[N:9]=[C:10]([N:11]3[CH2:16][CH2:15][N:14]([CH3:29])[C@@H:13]([CH2:17][CH2:18][O:19][CH3:20])[CH2:12]3)[C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 10043488(S)-2-methyl-11-[3-(2-methoxy-ethyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine

生成物 1

HCID 10090200(S)-2-Methyl-11-[3-(2-methoxy-ethyl)-4-methyl-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine収率 89%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

Combine (S)-2-methyl-11-[3-(2-methoxy-ethyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine (300.0 mg, 0.86 mmol), formaldehyde (76.4 μL, 0.94 mmol, 37% in water), and 1,2-dichloroethane (28.0 ml) and stir the mixture at ambient temperature for 5 minutes and add sodium triacetoxyborohydride (272.1 mg, 1.28 mmol). After stirring for 30 minutes at ambient temperature, quench the reaction with saturated sodium bicarbonate. Remove the organic portion, extract the aqueous with dichloromethane and combine, wash (brine), dry (sodium sulfate), and reduce the extracts to residue. Purify the residue on silica gel using dichloromethane/methanol (90:10) to give 260.4 mg (89%) of a yellow foam: mp=60° C., dec; mass spectrum (ion spray): m/z=365.2 (M+1).

後処理

  1. customquench
  2. customthe reaction with saturated sodium bicarbonate
  3. customRemove the organic portion
  4. extractionextract the aqueous with dichloromethane and combine
  5. washwash (brine)
  6. dry with materialdry (sodium sulfate)
  7. customPurify the residue on silica gel

出典と根拠

ORDレコード
ord-ceb78179fa2b42db89f686fdff220453
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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