Trifluoroacetic acid → HCID 66722638, compound

HRID 1639541Notes

Reaction equation

HRID 1639541 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[C:17]([N:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1)([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].N1CCOCC1.C(O)(C(F)(F)F)=O>CO.ClCCl>[C:20]([O:19][C:17]([N:24]1[CH2:29][CH2:28][C:27]2([NH:6][C:4](=[O:5])[C:3]3[CH:7]=[C:8]([N:11]4[CH2:12][CH2:13][O:14][CH2:15][CH2:16]4)[CH:9]=[CH:10][C:2]=3[O:1]2)[CH2:26][CH2:25]1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8083MorpholineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 66722929HCID 66722929, compound

Product 1

HCID 66722638HCID 66722638, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 50 mg (0.23 mmol) of 2-hydroxy-5-(morpholin-4-yl)benzamide, 59 mg (0.30 mmol) of 1-Boc-4-piperidone, and 40 μL of morpholine in 3 mL of MeOH is refluxed for 6 days. Removal of solvent by rotoevaporation and purification by preparative TLC gives 53 mg (0.13 mmol, 57% yield) of 1′-(tert-butyloxycarbonyl)-6-(morpholin-4-yl)spiro[1,3-benzoxazine-2,4′-piperidine]-4(3H)-one which on treatment with 40% TFA in dichloromethane at room temperature for 2 hr. gives the bis-TFA salt of 6-(morpholin-4-yl)spiro[1,3-benzoxazine-2,4′-piperidine]-4(3H)-one in quantitative yield.

Workup

  1. temperatureis refluxed for 6 days
  2. customRemoval of solvent
  3. customby rotoevaporation and purification by preparative TLC

Sources & evidence

ORD record
ord-b2e446263cc249f7bca1b26490715263
Source dataset
uspto-grants-2012_02
Patent number
US08110570B2

Reaction notes

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