Piperidine → HCID 11952155, compound

HRID 251447Notes

Reaction equation

HRID 251447 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[O:18][CH2:19][CH:20]([CH2:22]O)[N:21]=3)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.CS(Cl)(=O)=O.[NH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>O1CCCC1.N1CCCCC1>[N:36]1([CH2:22][CH:20]2[CH2:19][O:18][C:17]([C:14]3[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)=[CH:16][CH:15]=3)=[N:21]2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 8471Triethylamine3×HCID 31297Methanesulfonyl chlorideHCID 11950365HCID 11950365, compound

Product 1

HCID 11952155HCID 11952155, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-23 °C

Procedure

To a cold (−23° C.) solution of {2-[4-(3-piperidin-1-ylpropoxy)phenyl]-4,5-dihydro-1,3-oxazol-4-yl}methanol ax46 (0.27 g, 0.85 mmol, 1 eq) and triethylamine (0.413 ml, 2.98 mmol, 3.5 eq) in tetrahydrofuran (10 ml) is added methanesulfonyl chloride (0.23 ml, 2.98 mmol, 3.5 eq). The mixture is stirred for 2 h at −23° C., and then, concentrated under vacuum. The residual oil is treated with piperidine (0.08 ml, 0.8 nmol, 2 eq) and triethylamine (0.05 ml, 0.42 mmol, 1 eq) and stirred at 100° C. in a sealed tube overnight. After 24 h, piperidine (1 eq) and triethylamine (1 eq) are added and the mixture is stirred for another 48 h at 100° C. Concentration under vacuum gives 0.33 g of brown oil. The oil is purified on silicagel (eluent: dichloromethane/ethanol/ammonia 92:7.2:0.8) to give 45 mg of 1-(3-{4-[4-(piperidin-1-ylmethyl)-4,5-dihydro-1,3-oxazol-2-yl]phenoxy}propyl)piperidine 20.

Workup

  1. concentrationconcentrated under vacuum
  2. stirringstirred at 100° C. in a sealed tube overnight
  3. waitAfter 24 h
  4. stirringthe mixture is stirred for another 48 h at 100° C
  5. concentrationConcentration under vacuum

Sources & evidence

ORD record
ord-3e880abce2fe4ba8984329f1079d053c
Source dataset
uspto-grants-2011_01
Patent number
US07863450B2

Reaction notes

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