2-Morpholinoethylamine → Methyl 2-(2-morpholinoethylamino)-3-fluorobenzoate

HRID 1695940Notes

Reaction equation

F[C:2]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[O:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][NH2:21])[CH2:15][CH2:14]1>CN(C=O)C>[O:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][NH:21][C:2]2[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])[CH2:15][CH2:14]1

Participants

Conditions

Temperature: 100 °C

Procedure

Methyl 2,3-difluorobenzoate (817 mg, 4.746 mmol) and 2-morpholinoethanamine (2.5 mL, 19.20 mmol) were dissolved in DMF (15 mL) and heated in a microwave for 30 mins at 100° C. The crude material was purified by silica gel column chromatography with EtOAc/Hexanes to yield 943 mg (70%) of desired methyl 2-(2-morpholinoethylamino)-3-fluorobenzoate. LC/MS: 283.15 (M+1) Rt=1.48 min (10-90% 3/5 min (grad/run) with formic acid).

Workup

customThe crude material was purified by silica gel column chromatography with EtOAc/Hexanes

Sources & evidence

ORD record: ord-52f0ef9368a446deac9a8cac54bda3c5
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163737B2

Reaction notes

Loading…