N,N-Dimethylethylenediamine → HCID 46185757, compound

C-(3,4-Dihydro-2H-pyran-2-yl)-methylamine (free base) (13.3 g, 118 mmol) and 1,1′-carbonyl diimidazole (28.6 g, 176 mmol) were dissolved in dichloromethane (900 mL) and stirred for 2 h at room temperature. Under an Argon atmosphere N,N-Dimethyl ethylene diamine [51.2 mL, 470 mmol; dissolved in dichloromethane (250 mL)] was added and the reaction mixture stirred for 65 h at room temperature. The reaction mixture was concentrated to about one third volume under reduced pressure and extracted three times with water (100 mL). The organic layer was dried with sodium sulphate and the remaining solvent removed under reduced pressure to yield 1-[(R)-1-(3,4-Dihydro-2H-pyran-2-yl)methyl]-3-(2-dimethylamino-ethyl)urea (24.2 g, 91%) as pale yellow liquid. Analytical data 1-[(R)-1-(3,4-Dihydro-2H-pyran-2-yl)methyl]-3-(2-dimethylamino-ethyl)-urea: HPLC-MS: (M+H)+=228.2 at rt=1.155 min., column: Chromolith SpeedROD RP-18e 50-4, 6 mm; solvent A: water+0.1% TFA, solvent B: acetonitrile+0.1% TFA, gradient: 4% B at 0.0 min, 100% B at 2.6 min., 100% B at 3.3 min, flow: 2.4 mL/min., UV: 220 nm.

1. stirringthe reaction mixture stirred for 65 h at room temperature
2. concentrationThe reaction mixture was concentrated to about one third volume under reduced pressure
3. extractionextracted three times with water (100 mL)
4. dry with materialThe organic layer was dried with sodium sulphate
5. customthe remaining solvent removed under reduced pressure

ORD record

ord-a4b2fdc309d8430396db8fe76c3e9e06

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278454B2