Triethylamine → HCID 86756197, compound

HRID 564885Notes

Reaction equation

HRID 564885 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5](Cl)=[O:6].[CH3:12][C:13]1[CH:14]=[C:15]([CH:38]=[C:39]([CH3:41])[CH:40]=1)[C:16]([N:18]1[CH2:23][CH2:22][C@@H:21]([N:24]2[CH2:29][CH2:28][CH:27]([OH:30])[CH2:26][CH2:25]2)[CH2:20][C@@H:19]1[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:17].C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5]([O:30][CH:27]1[CH2:28][CH2:29][N:24]([C@@H:21]2[CH2:22][CH2:23][N:18]([C:16](=[O:17])[C:15]3[CH:14]=[C:13]([CH3:12])[CH:40]=[C:39]([CH3:41])[CH:38]=3)[C@@H:19]([CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:20]2)[CH2:25][CH2:26]1)=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 761913,5-Dichlorobenzoyl chlorideHCID 86756198HCID 86756198, compound

Product 1

HCID 86756197HCID 86756197, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,5-Dichlorobenzoyl chloride (1 g) was added to a mixture of compound 31 (2 g) and triethylamine (0.5 g) in CH2Cl2 (25 ml) and the mixture was stirred at RT for 1 hour. The mixture was washed with water. The organic layer was dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 97/3). The pure fractions were collected and their solvent evaporated. The residue was dried, yielding 0.34 g (11.7%) of (±)-trans-1-[1-(3,5-dimethylbenzoyl)-2-(phenylmethyl)-4-piperidinyl]-4-piperidinyl 3,5-dichloro-benzoate (compound 33, mp. 83.3° C.).

Workup

  1. washThe mixture was washed with water
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 97/3)
  6. customThe pure fractions were collected
  7. customtheir solvent evaporated
  8. customThe residue was dried

Sources & evidence

ORD record
ord-a79f69a1b34d453dbc043d312743a18d
Source dataset
uspto-grants-2001_01
Patent number
US06169097A

Reaction notes

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