Triethylamine → HCID 18700258, compound

HRID 2288724Notes

Reaction equation

HRID 2288724 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([C:13](Cl)=[O:14])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[Br:16][C:17]1[CH:29]=[CH:28][C:20]([O:21][CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:19][CH:18]=1.C(N(CC)CC)C>ClCCl>[Br:16][C:17]1[CH:29]=[CH:28][C:20]([O:21][CH:22]2[CH2:23][CH2:24][N:25]([C:13]([CH:10]3[CH2:11][CH2:12][N:7]([C:4]4[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=4)[CH2:8][CH2:9]3)=[O:14])[CH2:26][CH2:27]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 111837001-(4-Pyridinyl)-4-piperidinecarbonyl chlorideHCID 126455664-(4-Bromophenoxy)piperidine

Product 1

HCID 18700258HCID 18700258, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 1-(4-pyridyl)piperidine-4-carbonyl chloride (0.94 g) in dichloromethane (20 ml) was added slowly to a stirred solution of 4-(4-bromophenoxy)piperidine (1.0 g) and triethylamine (1.09 ml) in dichloromethane (10 ml) at 5° C. under an atmosphere of argon. The mixture was stirred at ambient temperature for 16 hours, and then the solvent was removed by evaporation. The residue was triturated with water. The resulting solid was collected by filtration and recrystallised from ethanol (10 ml) to give 4-(4-bromophenoxy)-1-[1-[4-pyridyl]piperidin-4-ylcarbonyl]piperidine (0.58 g) as an off-white solid, m.p. 127-130° C.;

Workup

  1. customthe solvent was removed by evaporation
  2. customThe residue was triturated with water
  3. filtrationThe resulting solid was collected by filtration
  4. customrecrystallised from ethanol (10 ml)

Sources & evidence

ORD record
ord-c87d9aeb943147dc99bf828b40a0d499
Source dataset
uspto-grants-2000_07
Patent number
US06090813

Reaction notes

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