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Tetrahydrofuran → N-Methyl-p-(1-adamantyloxy)aniline

HRID 2050208
Notes
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Reaction equation

HRID 2050208 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.[CH:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]23[CH2:31][CH:26]4[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]4)[CH2:23]2)[CH2:29]3)=[CH:17][CH:16]=1)=O.[OH-].[Na+]>O>[CH3:12][NH:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][C:22]23[CH2:31][CH:26]4[CH2:25][CH:24]([CH2:30][CH:28]([CH2:27]4)[CH2:29]2)[CH2:23]3)=[CH:19][CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 12510309N-Formyl-p-(1-adamantyloxy)anilineHCID 21226445Aluminium lithium hydride

Product 1

HCID 12510299N-Methyl-p-(1-adamantyloxy)aniline

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent
2×

Procedure

To a stirred suspension of 1.30 g. LiAlH4 in 20 ml. THF there was added 9.17 g. (0.034 mole) of N-formyl-p-(1-adamantyloxy)aniline in 200 ml. THF. Following 8 hours heating at reflux the mixture was cooled in ice and treated in turn with 1.3 ml. each of H2O and 15% NaOH and 4.9 ml. H2O. The inorganic gel was removed on a filter and the filtrate taken to dryness. The residue was recrystallized from Me2CO:SSB to give 5.96 g. (79%) of amine, N-methyl-p(1-adamantyloxy)aniline m.p. 134°-136°.

Workup

  1. additionTo a stirred suspension of 1.30 g
  2. temperatureheating
  3. temperatureat reflux the mixture
  4. temperaturewas cooled in ice
  5. additiontreated in turn with 1.3 ml
  6. customThe inorganic gel was removed on
  7. filtrationa filter
  8. customThe residue was recrystallized from Me2CO
  9. customSSB to give 5.96 g

Sources & evidence

ORD record
ord-878f01167a6a4ea79a551950c104e235
Source dataset
uspto-grants-1980_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04200588

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes