Piperidine → HCID 86673384, compound

HRID 1023350Notes

Reaction equation

HRID 1023350 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9]/[CH:10]=[CH:11]/[C:12]2[CH:41]=[CH:40][C:15]([CH2:16][N:17]3[CH2:22][CH2:21][N:20](C(OCC4C5C=CC=CC=5C5C4=CC=CC=5)=O)[CH2:19][CH2:18]3)=[CH:14][CH:13]=2)=[N:6][CH:7]=1.N1CCCCC1.[NH4+].[Cl-]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9]/[CH:10]=[CH:11]/[C:12]2[CH:13]=[CH:14][C:15]([CH2:16][N:17]3[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]3)=[CH:40][CH:41]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8082Piperidine2×HCID 25517Ammonium ChlorideHCID 86673385HCID 86673385, compound

Product 1

HCID 86673384HCID 86673384, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 9H-fluoren-9-ylmethyl 4-(4-{(E)-3-[(5-bromopyridin-2-yl)oxy]-prop-1-en-1-yl}benzyl)piperazine-1-carboxylate (0.604 g) in CH2Cl2 (10 mL) was added piperidine (0.196 mL). After stirring at room temperature for 1 hour, to the reaction mixture was added piperidine (0.784 mL) and stirred at room temperature for 4 hours. Then to the reaction mixture was added saturated aqueous NH4Cl and CH2Cl2. The organic layer was washed with saturated aqueous NH4Cl and saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was washed with Et2O to afford 1-(4-{(E)-3-[(5-bromopyridin-2-yl)oxy]prop-1-en-1-yl}benzyl)piperazine as a white powder (0.282 g).

Workup

  1. stirringstirred at room temperature for 4 hours
  2. washThe organic layer was washed with saturated aqueous NH4Cl and saturated aqueous NaCl
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. washThe residue was washed with Et2O

Sources & evidence

ORD record
ord-4711c652a28f45fd9a0718df05758429
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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