Methyl Ethyl Ketone → HCID 178424999, compound

HRID 634773Notes

Reaction equation

HRID 634773 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[CH2:20][CH2:19][C@H:18]([NH2:21])[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=1.CC(=O)CC>O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:15]2[CH2:20][CH2:19][C@H:18]([NH:21][CH2:29][CH2:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=3)[CH2:17][CH2:16]2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 140848591-(3-Bromopropyl)-4-methylbenzeneHCID 178511501HCID 178511501, compound

Product 1

HCID 178424999HCID 178424999, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of cis and trans 4-(4-benzyloxy-phenyl)-cyclohexyl-amine (preparation see under example 43a, 1.25 g, 4.44 mmol), K2CO3 (1.23 g, 8.88 mmol), 1-(3-Bromo-propyl)-4-methyl-benzene (1.18 g, 4.44 mmol) and 2-butanone was stirred at 80° for 48 h. Water was then added and the products were extracted with EtOAc. The organic layer was dried (Na2SO4), evaporated and the residue was purified by chromatography (SiO2, CH2Cl2—MeOH—aq. NH3 140:10:1) to give cis-[4-(4-benzyloxy-phenyl)-cyclohexyl]-(3-p-tolyl-propyl)-amine (180 mg; 10 %) as a light yellow solid (MS: m/e=414.4 (M+H+))and trans-[4-(4-benzyloxy-phenyl)-cyclohexyl]-(3-p-tolyl-propyl)-amine (38 mg; 2%) as a light yellow solid (MS: m/e=414.4 (M+H+)).

Workup

  1. extractionthe products were extracted with EtOAc
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated
  4. customthe residue was purified by chromatography (SiO2, CH2Cl2—MeOH—aq. NH3 140:10:1)

Sources & evidence

ORD record
ord-61a0451647fb4afcbc2188ae0c0c843a
Source dataset
uspto-grants-2001_02
Patent number
US06184236B2

Reaction notes

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