Dimethylformamide → N-(2-Butynyl)-N-methyl-p-(1-adamantyloxy)aniline

HRID 259357Notes

Reaction equation

HRID 259357 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]23[CH2:19][CH:14]4[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]4)[CH2:11]2)[CH2:17]3)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:27][C:28]#[C:29][CH3:30].CN(C=O)C>C1C=CC=CC=1>[CH2:27]([N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]23[CH2:11][CH:12]4[CH2:18][CH:16]([CH2:15][CH:14]([CH2:13]4)[CH2:19]2)[CH2:17]3)=[CH:7][CH:8]=1)[C:28]#[C:29][CH3:30]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27568621-Bromo-2-butyneHCID 12510299N-Methyl-p-(1-adamantyloxy)aniline

Product 1

HCID 20342180N-(2-Butynyl)-N-methyl-p-(1-adamantyloxy)aniline

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2.0 g. (0.0079 mole) of N-methyl-p-(1-adamantyloxyl)aniline, 1.07 g. K2CO3 and 1.03 g. of 1-bromo-2-butyne in 10 ml. DMF and 40 ml. C6H6 was heated at reflux for 17 hours. The mixture was allowed to cool and washed well with H2O and brine. The gum which remained when the organic layer was taken to dryness was dissolved in Et2O. The solid which precipitated on addition of HCl in Et2O was recrystallized from CH2Cl2 :EtOAc. There was obtained 2.09 g. (77%) of N-(2-butynyl)-N-methyl-p-(1-adamontyloxy)aniline, m.p. 180°-181°.

Workup

  1. additionA mixture of 2.0 g
  2. temperatureat reflux for 17 hours
  3. temperatureto cool
  4. washwashed well with H2O and brine
  5. dissolutionwas dissolved in Et2O
  6. customThe solid which precipitated on addition of HCl in Et2O
  7. customwas recrystallized from CH2Cl2
  8. customThere was obtained 2.09 g

Sources & evidence

ORD record
ord-e969392316154e53ad1937cda1749ea7
Source dataset
uspto-grants-1977_07
Patent number
US04036977

Reaction notes

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