Hydrochloric Acid → 4-(4-Hydroxy-4-tert-butylbenzylcyclohexylamino)-3-methoxy-2-methylpyridine

HRID 1008

Reaction equation

HRID 1008 reaction equation
[Mg].[C:2]([C:6]1[CH:13]=[CH:12][C:9]([CH2:10]Br)=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].O=[C:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]([CH3:28])[C:23]=2[O:29][CH3:30])[CH2:17][CH2:16]1.Cl.C1C[O:35]CC1>CCOCC>[OH:35][C:6]1([C:2]([CH3:5])([CH3:4])[CH3:3])[CH:13]=[CH:12][C:9]([CH2:10][N:21]([CH:18]2[CH2:19][CH2:20][CH2:15][CH2:16][CH2:17]2)[C:22]2[CH:27]=[CH:26][N:25]=[C:24]([CH3:28])[C:23]=2[O:29][CH3:30])=[CH:8][CH2:7]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 5462224MagnesiumHCID 196939514-(4-Oxocyclohexylamino)-3-methoxy-2-methylpyridine

Product 1

HCID 676711404-(4-Hydroxy-4-tert-butylbenzylcyclohexylamino)-3-methoxy-2-methylpyridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A Grignard solution is prepared from 1.2 g of magnesium and 12.9 g of 90% strength 4-tert-butylbenzyl bromide in 100 ml of abs. ether. 2.9 g of 4-(4-oxocyclohexylamino)-3-methoxy-2-methylpyridine in 50 ml of absolute THF are added dropwise to this solution. After 17 hours at room temperature it is acidified with 25 ml of 2N HCl, the mixture is extracted several times with ethyl acetate and the combined ethyl acetate phases are washed with sodium hydrogen carbonate solution. Purification is carried out by column chromatography on silica gel using ethyl acetate to which increasing amounts of methanol are added.

Workup

  1. extractionthe mixture is extracted several times with ethyl acetate
  2. washthe combined ethyl acetate phases are washed with sodium hydrogen carbonate solution
  3. customPurification
  4. temperatureincreasing amounts of methanol
  5. additionare added

Sources & evidence

ORD record
ord-77b579259b0e47c2ac2dc691717deb93
Source dataset
uspto-grants-1998_03
Patent number
US05723450

Linked notes

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