Isopropylamine → Agn-PC-0nhgeb

HRID 2219719Notes

Reaction equation

HRID 2219719 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-bae2e40662f840d5b2b1d2128cb243e7
Source dataset
uspto-grants-2008_08
Patent number
US07414076B2

Reaction notes

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