Methyl iodide → 4-[(Methoxymethyl)cyclobutyl]phenylamine

HRID 1246963Notes

Reaction equation

HRID 1246963 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH2:14][OH:15])[CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.[H-].[Na+].[CH3:18]I>C1COCC1>[CH3:18][O:15][CH2:14][C:10]1([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21906966HCID 21906966, compound

Product 1

HCID 219069604-[(Methoxymethyl)cyclobutyl]phenylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [(4-nitrophenyl)cyclobutyl]methane-1-ol (500 mg) and NaH (60% in mineral oil, 1.2 eq) and MeI (1.2 eq) in THF was stirred at RT overnight then quenched with H2O. The solution was extracted with EtOAc and washed with H2O followed by brine, dried over Na2SO4 and evaporated. The residue was mixed with Pd—C (10%, 100 mg) in EtOH (50 ml) and hydrogenated under H2 atmosphere for 30 min. The reaction was filtered through Celite and evaporated to give 4-[(methoxymethyl)cyclobutyl]phenylamine which used for next step without further purification.

Workup

  1. customthen quenched with H2O
  2. extractionThe solution was extracted with EtOAc
  3. washwashed with H2O
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. additionThe residue was mixed with Pd—C (10%, 100 mg) in EtOH (50 ml) and hydrogenated under H2 atmosphere for 30 min
  7. filtrationThe reaction was filtered through Celite
  8. customevaporated

Sources & evidence

ORD record
ord-d6f9769b7dea4d07861fd96eddddee47
Source dataset
uspto-grants-2006_10
Patent number
US07129252B2

Reaction notes

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