Hydrochloric Acid → 4-(Morpholin-2-yl)phenol

HRID 253011Notes

Reaction equation

HRID 253011 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N+](C1C=CC=CC=1S([O:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]2[O:31][CH2:30][CH2:29][N:28](S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)[CH2:27]2)=[CH:22][CH:21]=1)(=O)=O)([O-])=O.BrC1C=CC(S)=CC=1.Cl>CN(C)C=O>[NH:28]1[CH2:29][CH2:30][O:31][CH:26]([C:23]2[CH:24]=[CH:25][C:20]([OH:19])=[CH:21][CH:22]=2)[CH2:27]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 660494-BromothiophenolHCID 866312134-(4-(2-Nitrobenzenesulfonyl)morpholin-2-yl)phenyl 2-nitrobenzenesulfonate

Product 1

HCID 538045794-(Morpholin-2-yl)phenolYield 63.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (0.88 g, 6.33 mmol) was added to a solution of 1.16 g (2.11 mmol) of the title compound produced in step (iii) of Reference Example 12 in N,N-dimethylformamide (8.5 ml), and the mixture was stirred at room temperature for 5 min. Next, 1.20 g (6.33 mmol) of 4-bromobenzenethiol was added thereto, and the mixture was stirred at room temperature for 3.5 hr. The reaction was stopped by adding 1 N hydrochloric acid, and the reaction solution was adjusted to pH=3. The aqueous layer was washed with ethyl acetate and was concentrated to dryness under the reduced pressure. Methanol was added to the residue, and the mixture was filtered, The filtrate was concentrated under the reduced pressure, and the residue was purified by column chromatography on silica gel (chloroform:methanol=20:1, chloroform:methanol:28% aqueous ammonia=9:2:0.2) to give 240 mg (yield 63%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 3.5 hr
  2. washThe aqueous layer was washed with ethyl acetate
  3. concentrationwas concentrated to dryness under the reduced pressure
  4. additionMethanol was added to the residue
  5. filtrationthe mixture was filtered
  6. concentrationThe filtrate was concentrated under the reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (chloroform:methanol=20:1, chloroform:methanol:28% aqueous ammonia=9:2:0.2)

Sources & evidence

ORD record
ord-c791e66a12fc4a3aa48fc8ccb15ad938
Source dataset
uspto-grants-2011_01
Patent number
US07871982B2

Reaction notes

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