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

HRID 239784ノート

反応式

HRID 239784 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([NH2:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>C1(C)C=CC=CC=1>[CH3:8][C:9]1([NH:15][CH2:2][CH2:1][CH2:7][S:4]([OH:3])(=[O:6])=[O:5])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

参加物

4

反応物 2

HCID 14264Propane sultoneHCID 30215781-Amino-1-methylcyclohexane

生成物 1

HCID 160358483-[(1-Methylcyclohexyl)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 (5.00 g, 40 mmol) in toluene (10 mL) was added dropwise to a the crude solution of 1-methyl-1-cyclohexylamine in MTBK (total volume 30 mL). The mixture was heated to reflux for 18 hours then cooled to room temperature. The solid was collected by suction filtration, rinsed with acetone (2×8 mL). The solid was dried overnight at 45° C. in the vacuum oven. The title compound was obtained as a fine white solid (9.22 g). However, the proton NMR and the ES-MS were not clean. The solid was suspended in methanol (45 mL) and the suspension was warmed to reflux. Water (12 mL) was added dropwise until a clear yellow solution was obtained. The mixture was slowly cool to room temperature with stirring. The solid was collected by suction-filtration, rinsed with methanol (2×5 mL). Another crop was collected from the filtrate. Both crops were dried overnight at 45° C. in the vacuum oven. The title compound was obtained as a fine white solid (6.82 g, 29.0 mmol, 66% overall yield). Both crops were identical and were mixed for submitting the compound. 1H NMR (500 MHz, D2O) δ 1.04-1.11 (m, 1H), 1.19 (s, 3H), 1.31 (q, J=12.2 Hz, 2H), 1.40 (qt, J=12.2 Hz, 2H), 1.46-1.62 (m, 2H), 1.63 (br d, J=11.7 Hz, 2H), 1.94 (q, J=7.3 Hz, 2H), 2.86 (t, J=7.1 Hz, 2H), 3.03 (t, J=7.6 Hz, 2H); 13C NMR (125 MHz, D2O) δ 19.1, 21.5, 22.0, 24.6, 34.1, 39.1, 48.2, 60.2; ES-MS 236 (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 (2×8 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-889a94dab02948ceb223241479470ac1
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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