Water → benzyl 4-morpholinophenylcarbamate

HRID 245307Notes

Reaction equation

HRID 245307 reaction equation
C(=O)(O)[O-].[Na+].O.F[C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][C:14]=1[N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[NH2:11].[C:21](Cl)([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>CC(C)=O>[C:21]([NH:11][C:10]1[CH:12]=[CH:13][C:14]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:8][CH:9]=1)([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 14853303-Fluoro-4-morpholinoaniline

Product 1

HCID 2995703benzyl 4-morpholinophenylcarbamateYield 93.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

Sodium bicarbonate (17 g, 202 mmol) and 150 mL water were added to a solution of 3-fluoro-4-morpholinyl aniline (26 g, 133 mmol) of acetone (200 mL). The reaction mixture was cooled to −10˜0° C. Carbobenzoxy chloride (26 g. 152 mmol) was added dropwise within 1 hour. The mixture raised to room temperature (25° C.) naturally, and stirred at this temperature for 2 hours. Then the material liquid was poured into 500 mL ice water, filtered, and dried to provide 39 g of off-white solid in 90% yield.

Workup

  1. temperatureThe reaction mixture was cooled to −10˜0° C
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-a2a2d898f4d34457ab119df0f780fd2d
Source dataset
uspto-grants-2014_02
Patent number
US08658789B2

Reaction notes

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