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

HRID 239785Notes

Reaction equation

HRID 239785 reaction equation
[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

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 145933331-Methylcycloheptan-1-amine

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-0efdc8b39d5846808467cf1562290678
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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