Isopropylamine → Agn-PC-0nhgeb

HRID 239707

Reaction equation

HRID 239707 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[CH2:5]1[CH2:11][S:8](=[O:10])(=[O:9])[O:7][CH2:6]1.CCCCCC>ClCCl.CCOCC>[CH:1]([NH:4][CH2:6][CH2:5][CH2:11][S:8]([OH:10])(=[O:9])=[O:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 8058HexaneHCID 14264Propane sultone

Product 1

HCID 11194685Agn-PC-0nhgebYield 65.8%

Reagents, catalysts & solvents 1

HCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

Isopropylamine (2.5 mL, 29 mmol) was added to a solution of 1,3-propane sultone (3.05 g, 25 mmol) in a mixture of dichloromethane/ether (40 mL, 1:1). The mixture was heated at reflux for 3 hours. The reaction mixture was cooled to room temperature and hexane (10 mL) was added. The solid material was collected by filtration, rinsed with ether (10 mL), and dried in vacuo. Compound CG was obtained as a fine white powder (2.98 g, 65.6% yield). m.p. 240-43° C. 1H NMR (500 MHz, D2O) δ 1.06 (d, J=6.3 Hz, 6H), 1.86 (qt, J=7.6 Hz, 2H), 2.76 (t, J=7.6 Hz, 2H), 3.14 (t, J=7.8 Hz, 2H), 3.13-3.21 (m, J=6.6 Hz, 1H). 13C NMR (125 MHz, D2O) δ 18.2, 21.5, 25.8, 43.4, 47.9, 50.8.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. filtrationThe solid material was collected by filtration
  4. washrinsed with ether (10 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-f8b601054a0045a381270128927e6333
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Linked notes

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