HCID 18621513, compound → HCID 18621550, compound

HRID 324551Notes

Reaction equation

HRID 324551 reaction equation
Br.[OH:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[C:5]([CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:6]>Cl>[OH:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[C:5]([CH:7]1[CH2:12][CH2:11][N:10]([CH2:5][CH2:4][CH2:3][OH:2])[CH2:9][CH2:8]1)=[O:6]

Participants

3

Reactant 1

HCID 18621513HCID 18621513, compound

Product 1

HCID 18621550HCID 18621550, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4-(2-Hydroxybenzoyl)piperidine hydrobromide. An solution of 4-(2- and 4-hydroxybenzoyl)-1-acetyl piperidine (2.30 g, 9.30 mmol) in 6 N HCl (20 mL) was refluxed for 2 h. The cooled solution was extracted with ether (2×30 mL), made basic (NaOH) and was extracted with EtOAc (2×30 mL). An insoluble solid formed which was removed. The EtOAc portion was dried and was concentrated under reduced pressure. The free amine was dissolved in HBr (saturated solution in methanol, 5 mL) and the precipitated hydrobromide salt was collected, washed with ether (2×4 mL) and was dried in vacuo to afford the title compound as a colorless solid (0.26 g): mp 253° C. (dec); 1H NMR (DMSO-d6) d 1.60-1.83 (m, 2H), 1.94 (bd, J=12.9 Hz, 2H), 2.90-3.10 (m, 2H), 3.30 (bd, J=12.3 Hz, 2H), 3.65-3.90 (m, 1H), 6.94 (t, J=8.7 Hz, 2H), 7.50 (t, J =7.5 Hz, 1H), 7.88 (d, J=7.5 Hz, 1H), 8.33 (bs, 1H), 8.58 (bs, 1H), 11.63 (s, 1H).

Workup

  1. extractionThe cooled solution was extracted with ether (2×30 mL)
  2. extractionwas extracted with EtOAc (2×30 mL)
  3. customAn insoluble solid formed which
  4. customwas removed
  5. dry with materialThe EtOAc portion was dried
  6. concentrationwas concentrated under reduced pressure
  7. dissolutionThe free amine was dissolved in HBr (saturated solution in methanol, 5 mL)
  8. customthe precipitated hydrobromide salt was collected
  9. washwashed with ether (2×4 mL)
  10. customwas dried in vacuo

Sources & evidence

ORD record
ord-a31460a2c03349aab2107b5b11ecf0b7
Source dataset
uspto-grants-2001_04
Patent number
US06218404B1

Reaction notes

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