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Chloroacetyl chloride → 5-(Propan-2-yl)morpholin-3-one

HRID 359348
Notes
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Reaction equation

HRID 359348 reaction equation
[NH2:1][C@H:2]([CH2:6][OH:7])[CH:3]([CH3:5])[CH3:4].Cl[CH2:9][C:10](Cl)=[O:11]>C(O)C>[CH3:4][CH:3]([CH:2]1[NH:1][C:10](=[O:11])[CH2:9][O:7][CH2:6]1)[CH3:5]
ParticipantsProcedureSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 640993L-Valinol

Product 1

HCID 200638035-(Propan-2-yl)morpholin-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Treatment of valinol in basic ethanol with chloroacetyl chloride using the procedure of Surry, et. al., J. Am. Chem. Soc. (1955) 77, 633, gives 5-(2-propyl)-3-morpholinone. Deprotonation of the latter with NaH in DMF solution and reaction with methyl iodide gives the title compound.

Sources & evidence

ORD record
ord-e914668a7438475a80d2827f7442899a
Source dataset
uspto-grants-1991_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05001113

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes