Propane sultone → 3-[(1-Methylcycloheptyl)amino]propane-1-sulfonic acid

HRID 239785ノート

反応式

HRID 239785 の反応式
[CH2:1]1[CH2:7][S:4](=[O:6])(=[O:5])[O:3][CH2:2]1.[CH3:8][C:9]1([NH2:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>C1(C)C=CC=CC=1>[CH3:8][C:9]1([NH:16][CH2:2][CH2:1][CH2:7][S:4]([OH:3])(=[O:6])=[O:5])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

参加物

4

反応物 2

HCID 14264Propane sultoneHCID 145933331-Methylcycloheptan-1-amine

生成物 1

HCID 160359453-[(1-Methylcycloheptyl)amino]propane-1-sulfonic acid

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 1,3-propanesultone (4.3 g, 35 mmol) in toluene (10 mL) was added dropwise to a the crude solution of 1-methyl-1-cycloheptylamine in MTBK (total volume 30 mL). The mixture was heated to reflux for 18 hours then was cooled to room temperature. The solid was collected by suction filtration, rinsed with acetone (2×5 mL). The solid was dried overnight at 45° C. in the vacuum oven. The title compound was obtained as a fine white solid (7.77 g, 31.2 mmol, 80% overall yield). 1H NMR (500 MHz, D2O) δ 1.27 (s, 3H), 1.40-1.60 (m, 8H), 1.71-1.81 (m, 4H), 2.00-2.06 (m, 2H), 2.95 (t, J=6.3 Hz, 2H), 3.13 (t, J=7.1 Hz, 2H); 13C NMR (125 MHz, D2O) δ 22.0, 22.1, 23.3, 29.5, 37.1, 40.0, 48.3, 64.0; ES-MS 250(M+H)

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 18 hours
  3. filtrationThe solid was collected by suction filtration
  4. washrinsed with acetone (2×5 mL)
  5. customThe solid was dried overnight at 45° C. in the vacuum oven

出典と根拠

ORDレコード
ord-0efdc8b39d5846808467cf1562290678
出典データセット
uspto-grants-2014_02
特許番号
US08642801B2

反応ノート

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