Methanol → 4-(1-Adamantyloxy)-N-methyl-N-[3-(dimethylamino)propyl]aniline

HRID 2050210Notes

Reaction equation

HRID 2050210 reaction equation
CO.[CH3:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]23[CH2:21][CH:16]4[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]4)[CH2:13]2)[CH2:19]3)=[CH:7][CH:6]=1.[Li][CH2:23]CCC.Cl[CH:28]([N:31]([CH3:33])[CH3:32])[CH2:29]C>CCCCC.C1COCC1.C1(C)C=CC=CC=1>[C:12]12([O:11][C:8]3[CH:7]=[CH:6][C:5]([N:4]([CH3:23])[CH2:3][CH2:29][CH2:28][N:31]([CH3:33])[CH3:32])=[CH:10][CH:9]=3)[CH2:21][CH:16]3[CH2:15][CH:14]([CH2:20][CH:18]([CH2:17]3)[CH2:19]1)[CH2:13]2

Participants

8

Reactant 4

HCID 887MethanolHCID 12510299N-Methyl-p-(1-adamantyloxy)anilineHCID 22278018(1-Chloropropyl)dimethylamineHCID 178418339Butyllithium

Product 1

HCID 125103294-(1-Adamantyloxy)-N-methyl-N-[3-(dimethylamino)propyl]aniline

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice:MeOH cooled solution of 2.0 g. (0.078 mole) of N-methyl-p-(1-adamantyloxy)aniline in 20 ml. THF was added 4.75 ml. of 1.64 N BuLi in pentane. A solution of a 1:1 mixture of toluene and 1-chloro-N,N-dimethyl propyl amine in 20 ml. THF was then added and the mixture stirred at room temperature for 1 hour and at reflux for 20 hours. The bulk of the solvent was removed in vacuum and the residue dissolved in H2O and Et2O. The organic layer was washed with H2O and brine and taken to dryness. The residue was dissolved in CH2Cl2, treated with an excess of HCl in Et2O and taken to dryness. The remaining solid was recrystallized from MeOH:CH3CN to give 1.72 g. (53%) of 4'-(1-adamantyloxy)-N-methyl-N-[3-(dimethylamino)propyl]aniline, m.p. 221°-223°.

Workup

  1. temperatureat reflux for 20 hours
  2. customThe bulk of the solvent was removed in vacuum
  3. dissolutionthe residue dissolved in H2O
  4. washThe organic layer was washed with H2O and brine
  5. dissolutionThe residue was dissolved in CH2Cl2
  6. additiontreated with an excess of HCl in Et2O
  7. customThe remaining solid was recrystallized from MeOH
  8. customCH3CN to give 1.72 g

Sources & evidence

ORD record
ord-f52bc419c27943649cc63233a51eb0c4
Source dataset
uspto-grants-1980_04
Patent number
US04200588

Reaction notes

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