Acetic Acid → 4-(4-Methylmorpholin-2-yl)phenol

HRID 253012Notes

Reaction equation

HRID 253012 reaction equation
C=O.[C:3](O)(=O)C.[NH:7]1[CH2:12][CH2:11][O:10][CH:9]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH2:8]1>CO>[CH3:3][N:7]1[CH2:12][CH2:11][O:10][CH:9]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH2:8]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 712FormaldehydeHCID 538045794-(Morpholin-2-yl)phenol

Product 1

HCID 668627354-(4-Methylmorpholin-2-yl)phenolYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 36% aqueous formaldehyde solution (20.1 mg, 2.51 mmol), 0.029 ml (0.502 mmol) of acetic acid, and 53.2 mg (0.251 mmol) of triacetoxysodium borohydride were successively added to a solution of 15 mg (0.084 mmol) of the title compound produced in step (iv) of Reference Example 12 in methanol (0.7 ml), and the mixture was stirred at room temperature for 15 min. Thereafter, the reaction solution was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia=9:2:0.2) to give 15 mg (yield 93%) of the title compound.

Workup

  1. customThereafter, the reaction solution was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia=9:2:0.2)

Sources & evidence

ORD record
ord-090d6b78e50944f3a1435422802636a8
Source dataset
uspto-grants-2011_01
Patent number
US07871982B2

Reaction notes

Loading…