Dichloromethane → {4-[4-(4-Aminobutyl)phenyl]butyl}carbamic acid benzyl ester

HRID 1696851ノート

反応式

HRID 1696851 の反応式
[CH2:1]([O:8][C:9](=[O:36])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][N:25]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN.C(Cl)Cl>C(O)C>[CH2:1]([O:8][C:9](=[O:36])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][NH2:25])=[CH:17][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 9321HydrazineHCID 66860915(4-{4-[4-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)butyl]phenyl}butyl)carbamic acid benzyl ester

生成物 1

HCID 58100085{4-[4-(4-Aminobutyl)phenyl]butyl}carbamic acid benzyl ester収率 206.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution containing 59 (4.0 g, 8.20 mmol) and hydrazine (2.06 g, 41.20 mmol) dissolved in ethanol (50 mL) and methylene chloride (10 mL) was heated to reflux. The reaction mixture was allowed to stir for 16 h under N2 atmosphere. The solution was filtered and the filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography eluting with a mixture of 0-20% (10% concentrated ammonium hydroxide in methanol) and dichloromethane to afford the desired product 7 (6.00 g, 72%) as an off white solid: 1H NMR (300 MHz, CDCl3) δ 7.34 (s, 4H), 7.07 (s, 4H), 5.08 (s, 2H), 3.18 (t, 2H), 2.94 (s, 2H), 2.70 (t, 2H), 2.59 (t, 4H), 1.65-1.47 (m, 5H); m/z (ESI) 355 [C22H30N2O2+H]+.

後処理

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe resulting residue was purified by column chromatography
  4. washeluting with a mixture of 0-20% (10% concentrated ammonium hydroxide in methanol) and dichloromethane

出典と根拠

ORDレコード
ord-6707dc3f65424cb5b3195ce19164ad24
出典データセット
uspto-grants-2012_04
特許番号
US08163758B2

反応ノート

読み込み中…