Methylamine → HCID 178484787, compound

HRID 657620Notes

Reaction equation

HRID 657620 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:15][NH2:16]>O1CCCC1>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([NH:16][CH3:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 45989164-(4'-Hydroxyphenyl)cyclohexanone

Product 1

HCID 178484787HCID 178484787, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 4-(4-hydroxyphenyl)cyclohexanone (3 g) in tetrahydrofuran (20 mL) and a solution of methylamine in tetrahydrofuran (7.9 mL, 2 M) is stirred overnight at room temperature, concentrated under reduced pressure, dissolved in a mixture of dichloromethane and methanol (30 mL, 1/1) and cooled at a temperature close to 0° C. Sodium borohydride (822 mg) is added portionwise and the mixture is stirred at room temperature for one hour. The precipitate is filtered and washed with diethyl oxide to give 1.1 g of trans-4-(4-hydroxyphenyl)-N-methylcyclohexanamine used without further purification.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutiondissolved in a mixture of dichloromethane and methanol (30 mL, 1/1)
  3. temperaturecooled at a temperature
  4. customclose to 0° C
  5. additionSodium borohydride (822 mg) is added portionwise
  6. filtrationThe precipitate is filtered
  7. washwashed with diethyl oxide

Sources & evidence

ORD record
ord-0ebd773531b94e4ba5897da57d3ca3b5
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

Loading…