Triethylamine → 7-[[4-(2,6-Dichlorophenyl)-1-piperidinyl]carbonyl]-6,7,8,9-tetrahydro-1-methyl-5H-benzocyclohepten-5-one

HRID 1241882Notes

Reaction equation

HRID 1241882 reaction equation
[CH3:1][C:2]1[C:7]2[CH2:8][CH2:9][CH:10]([C:14]([OH:16])=O)[CH2:11][C:12](=[O:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.Cl.[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:26]=1[CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.C(N(CC)CC)C>C(Cl)Cl.O>[CH3:1][C:2]1[C:7]2[CH2:8][CH2:9][CH:10]([C:14]([N:35]3[CH2:34][CH2:33][CH:32]([C:26]4[C:25]([Cl:24])=[CH:30][CH:29]=[CH:28][C:27]=4[Cl:31])[CH2:37][CH2:36]3)=[O:16])[CH2:11][C:12](=[O:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 11229708HCID 11229708, compoundHCID 219369304-(2,6-dichloro-phenyl)-piperidine hydrochloride

Product 1

HCID 219369597-[[4-(2,6-Dichlorophenyl)-1-piperidinyl]carbonyl]-6,7,8,9-tetrahydro-1-methyl-5H-benzocyclohepten-5-oneYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

1 g (4.58 mmol) of (±)-1-methyl-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene-7-carboxylic acid was dissolved in 40 mL of dry CH2Cl2 and 1.2 mL (13.74 mmol) of oxalyl chloride were added dropwise at 0° C. under a nitrogen atmosphere. The solution was allowed to warm to room temperature overnight, then the solvent and the excess oxalyl chloride were removed in vacuo. The resulting acyl chloride was dissolved in 20 mL of dry CH2Cl2 and added to a solution of 1.22 g (4.58 mmol) of 4-(2,6-dichloro-phenyl)-piperidine hydrochloride and 1.91 mL (13.74 mmol) of triethylamine in 30 mL of dry CH2Cl2 at 0° C. The reaction mire was allowed to warm to room temperature overnight, water was added, the organic phase was collected, washed with 1 N HCl solution and dried. The solvent was removed in vacuo and the resulting crude product was purified by flash chromatography, eluting with a mixture Et2O/Hexane 8:2 respectively, yielding 1.4 g of the title compound.

Workup

  1. customthe solvent and the excess oxalyl chloride were removed in vacuo
  2. dissolutionThe resulting acyl chloride was dissolved in 20 mL of dry CH2Cl2
  3. temperatureto warm to room temperature overnight
  4. customthe organic phase was collected
  5. washwashed with 1 N HCl solution
  6. customdried
  7. customThe solvent was removed in vacuo
  8. customthe resulting crude product was purified by flash chromatography
  9. washeluting with a mixture Et2O/Hexane 8:2 respectively

Sources & evidence

ORD record
ord-cffcfb8c3f224bb2bf84760cc556b93d
Source dataset
uspto-grants-2006_10
Patent number
US07115633B2

Reaction notes

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