Desipramine → {2-[3-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-propylamino]-ethyl]-carbamic Acid tert-butyl Ester

HRID 840511

反応式

HRID 840511 の反応式
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][N:6]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH2:14][CH2:13][C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]1=2.C(=O)([O-])[O-].[K+].[K+].[C:27]([NH:34][CH2:35]CBr)([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].[I-].[Na+]>C1OCCOCCOCCOCCOCCOC1.CN(C)C=O.CC(C)=O>[C:30]([O:29][C:27](=[O:28])[NH:34][CH2:35][CH2:1][NH:2][CH2:3][CH2:4][CH2:5][N:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=2[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]1=2)([CH3:33])([CH3:32])[CH3:31]

参加物

8

反応物 4

HCID 2995DesipramineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

生成物 1

HCID 86757926{2-[3-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-propylamino]-ethyl]-carbamic Acid tert-butyl Ester収率 97.2%

試薬・触媒・溶媒 3

HCID 2855718-Crown-6触媒HCID 180Acetone溶媒HCID 6228Dimethylformamide溶媒

実験手順

To 3.23 g (12.04 mmol) of desipramine free base was added 80 ml of dry acetone, 3.6 g of anhydrous potassium carbonate, 3.0 g (13.45 mmol) of 2-(BOC-amino) ethyl bromide, 3 ml of anhydrous dimethylformamide, 15 mg of 18-crown-6 and 500 mg of sodium iodide. The mixture was allowed to reflux 18 hours under argon atmosphere. The reaction mixture was cooled to room temperature and filtered. The residue was washed with 10 ml of acetone. The filtrate was concentrated and the residue was purified by silica gel column chromatography using 4% methanol in ethyl acetate to give 4.8 g (11.7 mmol, 96%) of 23 as a thick oil.

後処理

  1. temperatureto reflux 18 hours under argon atmosphere
  2. filtrationfiltered
  3. washThe residue was washed with 10 ml of acetone
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-45a1cb867cff4c698d001297c3c0a26d
出典データセット
uspto-grants-2002_04
特許番号
US06368814B1

関連ノート

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