Triethylamine → HCID 22273746, compound

HRID 1064377Notes

Reaction equation

HRID 1064377 reaction equation
[CH:1]1[C:6]2[CH2:7][CH2:8][CH:9]([C:13]([OH:15])=O)[CH2:10][C:11](=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1.O=S(Cl)Cl.[C:20]1([CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>C(Cl)Cl>[C:20]1([CH:26]2[CH2:27][CH2:28][N:29]([C:13]([CH:9]3[CH2:8][CH2:7][C:6]4[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=4[C:11](=[O:12])[CH2:10]3)=[O:15])[CH2:30][CH2:31]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 698734-PhenylpiperidineHCID 22273758HCID 22273758, compound

Product 1

HCID 22273746HCID 22273746, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.3 g (1.47 mmol) of (±)-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one-7-carboxylic acid in 5 mL of CH2Cl2 were added, at 0° C., 0.27 mL (3.69 mmol) of SOCl2 and the solution was warmed at 50° C. for 20 min. The solvent and the excess SOCl2 were removed in vacuo and the resulting residue was redissolved in 5 mL of CH2Cl2. 0.24 g (1.47 mmol) of 4-phenylpiperidine and 0.2 mL (1.47 mmol) of triethylamine dissolved in 5 mL of CH2Cl2 were added at room temperature to this solution; the stirring was continued overnight, then the solvent was removed in vacuo and the residue was taken up in AcOEt; the organic phase was washed successively with 10% NaOH, 10% HCl and water, the solvent was removed in vacuo yielding 0.49 g of the title compound as an oil which was used without further purification.

Workup

  1. customThe solvent and the excess SOCl2 were removed in vacuo
  2. dissolutionthe resulting residue was redissolved in 5 mL of CH2Cl2
  3. additionwere added at room temperature to this solution
  4. customthe solvent was removed in vacuo
  5. washthe organic phase was washed successively with 10% NaOH, 10% HCl and water
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-9f6eb835b9454107a949982a26946e3c
Source dataset
uspto-grants-2005_11
Patent number
US06969724B2

Reaction notes

Loading…