1,2-Dichloroethane → N-(1-(4-(4-chlorophenyl)piperidin-1-yl)-3-methyl-1-oxobutan-2-yl)-2-phenylacetamide

HRID 1016093Notes

Reaction equation

HRID 1016093 reaction equation
C1C=CC2N(O)N=NC=2C=1.[C:11]1([CH2:17][C:18]([OH:20])=O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(Cl)CCl.Cl.[NH2:26][CH:27]([CH:43]([CH3:45])[CH3:44])[C:28]([N:30]1[CH2:35][CH2:34][CH:33]([C:36]2[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=2)[CH2:32][CH2:31]1)=[O:29]>CN(C=O)C.CCN(C(C)C)C(C)C.CO>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([CH:33]2[CH2:32][CH2:31][N:30]([C:28](=[O:29])[CH:27]([NH:26][C:18](=[O:20])[CH2:17][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:43]([CH3:45])[CH3:44])[CH2:35][CH2:34]2)=[CH:37][CH:38]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 999Phenylacetic AcidHCID 757711-HydroxybenzotriazoleHCID 672994912-Amino-1-(4-(4-chlorophenyl)piperidin-1-yl)-3-methylbutan-1-one hydrochloride

Product 1

HCID 24758856N-(1-(4-(4-chlorophenyl)piperidin-1-yl)-3-methyl-1-oxobutan-2-yl)-2-phenylacetamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

A reaction tube was charged with HOBt (10 mg), phenylacetic acid (12 mg) and EDC (14 mg) in DMF (0.7 mL). The resulting mixture was agitated at rt. for 15 min, and then a solution of 2-amino-1-(4-(4-chlorophenyl)piperidin-1-yl)-3-methylbutan-1-one hydrochloride (20 mg) in DIEA (50 μL) and DMF (250 μL) was added and the resulting mixture was shaken overnight at rt. At the conclusion of this period, the resulting solution was diluted with MeOH and purified by preparative LC-MS to provide Example 9. MS found: (M+H)+=414.

Workup

  1. stirringthe resulting mixture was shaken overnight at rt
  2. custompurified by preparative LC-MS
  3. customto provide Example 9

Sources & evidence

ORD record
ord-389a42b0707243d6bef34c724bbbacf7
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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