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

HRID 259359Notes

Reaction equation

HRID 259359 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 1.64N 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-e0b009c0adc941c99fcd5421d8dc9c14
Source dataset
uspto-grants-1977_07
Patent number
US04036977

Reaction notes

Loading…