Morpholine → HCID 4268755, compound

HRID 2200568Notes

Reaction equation

HRID 2200568 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=O.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.[BH4-].[Na+]>CO.C(O)(=O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH2:4][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 4311764Sodium borohydrideHCID 212945242-Chloro-5-hydroxybenzaldehyde2×

Product 1

HCID 4268755HCID 4268755, compoundYield 51.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 2-chloro-5-hydroxybenzaldehyde (200 mg, 1.27 mmol, intermediate 28a) and morpholine (280 mg, 3.21 mmol) in methanol (10 mL) was added 2 drops of acetic acid and the mixture was stirred at room temperature for 2 h. To the mixture, sodium borohydride (97 mg, 2.56 mmol) was added and the resulting mixture was stirred at room temperature for 4 h. The mixture was quenched with dilute hydrochloride acid and concentrated to give crude product. This crude material was purified by silica gel chromatography eluting with petroleum ether/ethyl acetate (5:1 to 1:1) to give 4-chloro-3-(morpholinomethyl)phenol (150 mg, 51.8% yield) as white solid. LCMS retention time 0.378; LCMS MH+ 228.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 4 h
  2. customThe mixture was quenched with dilute hydrochloride acid
  3. concentrationconcentrated
  4. customto give crude product
  5. customThis crude material was purified by silica gel chromatography
  6. washeluting with petroleum ether/ethyl acetate (5:1 to 1:1)

Sources & evidence

ORD record
ord-0377936147f54b89926a4fac82eecc35
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

Loading…