Tert-Butylamine → 28225-89-0

HRID 1657629Notes

Reaction equation

HRID 1657629 reaction equation
[C:1]([C:3]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:4]=1[O:5][CH2:6][CH:7]1[O:9][CH2:8]1)#[N:2].C(C1C(C)=CC=CC=1O)#N.C(C1OC1)[Cl:26].[C:30]([NH2:34])([CH3:33])([CH3:32])[CH3:31]>[OH-].[Na+].CO>[ClH:26].[C:1]([C:3]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:4]=1[O:5][CH2:6][CH:7]([OH:9])[CH2:8][NH:34][C:30]([CH3:33])([CH3:32])[CH3:31])#[N:2]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 7835EpichlorohydrinHCID 128585482-Hydroxy-6-methylbenzonitrileHCID 21424198HCID 21424198, compound

Product 1

HCID 2142421328225-89-0

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

1-(2-Cyano-3-methyl-phenoxy)-2,3-epoxy propane, prepared from 17 gm (0.128 mol) of 2-cyano-3-methylphenol and 12.2 gm (0.132 mol) of epichlorohydrin in 125 ml of 1 N NaOH, was dissolved as a dark, impure viscous oil in 200 ml of methanol, and 29 ml of tert.-butylamine were added thereto. After refluxing the mixture for 2 hours, the solvent was distilled off under vacuum, and the brown residue was extracted with dilute HCl. The clear solution was filtered over charcoal and was made alkaline with NaOH. The precipitating base was taken up in ether and the organic phase was separated and was washed repeatedly with water and dried over MgSO4. After concentration up to weight constancy, 4.5 gm of a base remained and this was dissolved in a small amount of ethanol. The hydrochloride salt was precipitated by an addition of ethereal HCl and was isolated as a solid product. It was recrystallized from acetonitrile with an addition of ether followed by a second recrystallization from ethanol with an addition of ether to obtain 1-(2-cyano-3-methyl-phenoxy)-2-hydroxy-3-tert.-butylamino propane hydrochloride having a melting point of 178°-180°C. Using this same procedure, there was obtained 1-(2-cyanomethyl-3-methyl-phenoxy)-2-hydroxy-3-tert.-butylamino-propane hydrochloride.

Workup

  1. temperatureAfter refluxing the mixture for 2 hours
  2. distillationthe solvent was distilled off under vacuum
  3. extractionthe brown residue was extracted with dilute HCl
  4. filtrationThe clear solution was filtered over charcoal
  5. customthe organic phase was separated
  6. washwas washed repeatedly with water
  7. dry with materialdried over MgSO4
  8. concentrationAfter concentration up
  9. dissolutionthis was dissolved in a small amount of ethanol
  10. customThe hydrochloride salt was precipitated by an addition of ethereal HCl
  11. customwas isolated as a solid product
  12. customIt was recrystallized from acetonitrile with an addition of ether
  13. customfollowed by a second recrystallization from ethanol with an addition of ether

Sources & evidence

ORD record
ord-8d2d00252b2c46edbeeca3084af597ef
Source dataset
uspto-grants-1976_06
Patent number
US03961071

Reaction notes

Loading…