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Acetic Acid → 3,4-dihydro-6-(1,1-dimethylethyl)-8-iodo-1'-methylspiro[2H-1,3-benzoxazin-2,4'-piperidine]

HRID 372831
Notes
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Reaction equation

HRID 372831 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:6]=[C:5]([I:13])[C:4]=1[OH:14].[CH3:15][N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.C(O)(=O)C>C1C=CC=CC=1>[CH3:12][C:9]([C:7]1[CH:6]=[C:5]([I:13])[C:4]2[O:14][C:19]3([CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]3)[NH:1][CH2:2][C:3]=2[CH:8]=1)([CH3:11])[CH3:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 740491-Methyl-4-piperidoneHCID 1192862-Aminomethyl-4-t-butyl-6-iodophenol

Product 1

HCID 128579003,4-dihydro-6-(1,1-dimethylethyl)-8-iodo-1'-methylspiro[2H-1,3-benzoxazin-2,4'-piperidine]Yield 57.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-aminomethyl-4-(1,1-dimethylethyl)-6-iodophenol (6.0 g., 0.02 mole), 1-methyl-4-piperidone (2.24 g., 0.02 mole), acetic acid (2 ml.) and benzene (100 ml.) is refluxed under a Dean-Stark trap for 4 hrs. The clear yellow solution then is washed with 2% sodium hydroxide solution, water and salt brine and dried (MgSO4). The residue that remains after evaporation of the benzene is crystallized from ethanol to obtain 3,4-dihydro-6-(1,1-dimethylethyl)-8-iodo-1'-methylspiro[2H-1,3-benzoxazin-2,4'-piperidine], (4.6 g.), m.p. 155°-156.5° C.

Workup

  1. temperatureis refluxed under a Dean-Stark trap for 4 hrs
  2. washThe clear yellow solution then is washed with 2% sodium hydroxide solution, water and salt brine
  3. dry with materialdried (MgSO4)
  4. customafter evaporation of the benzene
  5. customis crystallized from ethanol

Sources & evidence

ORD record
ord-d7b212be02cb4b459c195496c9ce6734
Source dataset
uspto-grants-1978_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04092414

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes