Piperidine → 1-({2-[4-(3-Chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}acetyl)piperidine

HRID 1710795Notes

Reaction equation

HRID 1710795 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([CH2:18][C:19]([OH:21])=O)=[C:15]([CH3:17])[N:16]=2)=[CH:8][CH:7]=1.C(N(CC)CC)C.[NH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>ClCCl>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[S:13][C:14]([CH2:18][C:19]([N:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)=[O:21])=[C:15]([CH3:17])[N:16]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 5

HCID 8082PiperidineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59457516{2-[4-(3-Chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}acetic acid

Product 1

HCID 594575031-({2-[4-(3-Chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}acetyl)piperidineYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of {2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}acetic acid i103 (0.5 g, 1.41 mmol, 1 eq), triethylamine (0.2 ml, 1.41 mmol, 1 eq), and piperidine (0.15 ml, 1.45 mmol, 1.03 eq) in dichloromethane (30 ml) is cooled (ice bath) and treated with 1-hydroxybenzotriazole (38 mg, 0.28 mmol, 0.2 eq) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (0.271 g, 1.41 mmol, 1 eq). The mixture is stirred at room temperature overnight, then diluted with 70 ml of dichloromethane. The organic layer is washed with water (2×50 ml), brine, dried over magnesium sulfate and filtered. The solvent is removed under reduced pressure to obtain an orange solid. The solid is triturated in acetonitrile, filtered and rinsed with cold diethyl ether to give 0.18 g of 1-({2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}acetyl)piperidine i104 as a yellow solid.

Workup

  1. washThe organic layer is washed with water (2×50 ml), brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent is removed under reduced pressure
  5. customto obtain an orange solid
  6. customThe solid is triturated in acetonitrile
  7. filtrationfiltered
  8. washrinsed with cold diethyl ether

Sources & evidence

ORD record
ord-e8a27378bfa94504a93f421f510cd8cd
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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