Diisopropylethylamine → Tert-butyl 4-[4-(cyclopropylmethylcarbamoyl)-phenyl]-piperidine-1-carboxylate

HRID 405940

Reaction equation

HRID 405940 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([OH:3])=O.C(N(C(C)C)CC)(C)C.CN(C(ON1N=[N:47][C:42]2[CH:43]=[CH:44][CH:45]=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.C1(CN)CC1>CN(C)C=O>[CH:43]1([CH2:42][NH:47][C:1]([C:4]2[CH:5]=[CH:6][C:7]([CH:10]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:12][CH2:11]3)=[CH:8][CH:9]=2)=[O:3])[CH2:45][CH2:44]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 81671(Cyclopropylmethyl)ammonium chlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 224928594-(4-Carboxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 66724516Tert-butyl 4-[4-(cyclopropylmethylcarbamoyl)-phenyl]-piperidine-1-carboxylateYield 81.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

500 mg tert-butyl 4-(4-carboxyphenyl)-piperidine-1-carboxylate are placed in 28 ml dimethylformamide, then 1.14 ml diisopropylethylamine and 747 mg HATU are added. The reaction mixture is stirred for 15 min at ambient temperature, then 194 mg cyclopropylmethylamin hydrochloride are added. The reaction mixture is stirred overnight at ambient temperature. Then the product is purified by preparative HPLC (method A). 480 mg product are obtained as an oil. Analytical HPLC-MS (method B): RT=1.64 min.

Workup

  1. stirringThe reaction mixture is stirred overnight at ambient temperature
  2. customThen the product is purified by preparative HPLC (method A)

Sources & evidence

ORD record
ord-3855d6e98a474ca0b4ab0e99fbd46366
Source dataset
uspto-grants-2014_06
Patent number
US08754073B2

Linked notes

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