Aminoethyl sulfate → HCID 22674745, compound

HRID 1006319Notes

Reaction equation

[CH:1]([CH:14]1[CH2:16][O:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(O[CH2:22][CH2:23][NH2:24])(O)(=O)=O>C(O)(C)C.[OH-].[Na+]>[CH:1]([CH:14]1[O:15][CH2:22][CH2:23][NH:24][CH2:16]1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 2-benzhydryloxirane (631 mg) in isopropyl alcohol (4 ml) was added portionwise to a stirred solution of 2-aminoethyl hydrogensulfate (2.12 g) in a mixture of 20% sodium hydroxide solution (3 ml) at 50° C. The whole was stirred at 100° C. for 6 hours and thereto 40% sodium hydroxide solution (6 ml) was added at 100° C. After being stirred for 18 hours at the same temperature, the mixture was partitioned between ethyl acetate and 2N sodium hydroxide. The organic layer was separated, washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel using a mixed solvent of dichloromethane and methanol (20:1) to give 2-benzhydrylmorpholine (102 mg) as a colorless powder.

Workup

stirringAfter being stirred for 18 hours at the same temperature
customthe mixture was partitioned between ethyl acetate and 2N sodium hydroxide
customThe organic layer was separated
washwashed with brine
dry with materialdried over sodium sulfate
customevaporated under reduced pressure
customThe resulting residue was purified by column chromatography on silica gel using a mixed solvent of dichloromethane and methanol (20:1)

Sources & evidence

ORD record: ord-9c78486b5fe440378754be9444316a67
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06787543B2

Reaction notes

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