Piperidine → HCID 59457505, compound

HRID 1710762Notes

Reaction equation

HRID 1710762 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:17][CH:18]=[C:19]([CH2:21][C:22]([OH:24])=O)[N:20]=2)=[CH:12][CH:11]=1.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>ClCCl>[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:17][CH:18]=[C:19]([CH2:21][C:22]([N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:24])[N:20]=2)=[CH:12][CH:11]=1

Participants

7

Reactant 5

HCID 8082PiperidineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59457491HCID 59457491, compound

Product 1

HCID 59457505HCID 59457505, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2-{4-[2-(2-methylpyrrolidin-1-yl)ethoxy]phenyl}-1,3-oxazol-4-yl)acetic acid i53 (0.29 g, 0.87 mmol, 1 eq), piperidine (0.18 ml, 1.75 mmol, 2 eq) and triethylamine (0.36 ml, 3.6 mmol, 3 eq) in dichloromethane (20 ml) is cooled to 0° C. N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.42 g, 2.17 mmol, 2.5 eq) and 1-hydroxybenzotriazole (0.12 g, 0.87 mmol, 1 eq) are then added. The mixture is stirred 24 h at room temperature, and washed two times with a saturated solution of aqueous ammonium chloride. The organic layer is dried over magnesium sulfate, filtered and concentrated under vacuum. Purification by chromatography over silicagel (eluent: dichloromethane/methanol/ammonia 97/2.7/03) affords 0.15 g of 1-[(2-{4-[2-(2-methylpyrrolidin-1-yl)ethoxy]phenyl}-1,3-oxazol-4-yl)acetyl]piperidine i54.

Workup

  1. washwashed two times with a saturated solution of aqueous ammonium chloride
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customPurification by chromatography over silicagel (eluent: dichloromethane/methanol/ammonia 97/2.7/03)

Sources & evidence

ORD record
ord-7c91c32877a34195b2512bd3ff80f387
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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