Piperidine → HCID 35752662, compound

HRID 1592764Notes

Reaction equation

HRID 1592764 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([OH:22])=O)[CH2:10][CH2:9]1)(OC(C)(C)C)=O.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[N:11]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:22])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27567762-[4-(tert-Butoxycarbonyl)piperazin-1-yl]benzoic acid

Product 1

HCID 35752662HCID 35752662, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The 1-Boc-4-(2-carboxy-phenyl)-piperazine (1 g, 3.26 mmol), piperidine (278 mg, 3.26 mmol), EDCI (625 mg, 3.26 mmol) and DMAP (50 mg, catalytic) were dissolved in DCM (20 mL) and stirred at r.t. for about 12 hours. The mixture was washed with water, dried, filtered, and concentrated. The resultant foam was taken up in DCM (10 mL) and TPA (5 mL) was added, and the mixture stirred at r.t. for about 2 hours. The reaction was concentrated and subjected to SCX ion exchange chromatography followed by silica gel chromatography to afford the final product (868 mg, 71%) as a white foam. LRMS (ESI+): 274.1 (M+1).

Workup

  1. washThe mixture was washed with water
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionTPA (5 mL) was added
  6. stirringthe mixture stirred at r.t. for about 2 hours
  7. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-fc109c5f4a5748f9b31ba52de51b3f47
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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