Methyl iodide → HCID 178503944, compound

HRID 1016111Notes

Reaction equation

HRID 1016111 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:31])[C@H:15]([NH:19][C:20]([NH:22][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[S:21])[CH:16]([CH3:18])[CH3:17])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:32]([O-])([O-])=O.[K+].[K+].CI>CC#N.CCOCC>[C:23](/[N:22]=[C:20](\[S:21][CH3:32])/[NH:19][C@H:15]([CH:16]([CH3:17])[CH3:18])[C:14]([N:11]1[CH2:10][CH2:9][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:13][CH2:12]1)=[O:31])(=[O:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57888658HCID 57888658, compound

Product 1

HCID 178503944HCID 178503944, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of (R)—N-(1-(4-(4-chlorophenyl)piperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamothioyl)benzamide (300 mg, crude) in CH3CN (2 mL) was added K2CO3 (275 mg, 2 mmol) followed by MeI (75 μL, 2 mmol). The reaction was stirred for 4 h at rt., diluted with Et2O (10 mL) and the solids were filtered through a plug of celite. The filtrate was condensed in vacuo to give (R,Z)-methyl N′-benzoyl-N-(1-(4-(4-chlorophenyl)piperidin-1-yl)-3-methyl-1-oxobutan-2-yl)carbamimidothioate (300 mg, m/z 473, M+1) as a foam, which was used in subsequent steps without purification.

Workup

  1. filtrationthe solids were filtered through a plug of celite
  2. customcondensed in vacuo

Sources & evidence

ORD record
ord-9c8ae9cf9a1440f68cb9d6c2265a3ee8
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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