Piperidine → HCID 20536433, compound

HRID 1156127Notes

Reaction equation

HRID 1156127 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].C(N(CC)CC)C.[NH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.[H][H]>O1CCCC1.CCOCC>[F:1][C:2]1[CH:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:8]=[CH:7][C:3]=1[C:4]([N:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)=[O:5]

Participants

7

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 20536424HCID 20536424, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20536433HCID 20536433, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a warm solution of N-carbobenzoyloxy-[2-fluoro-4-(hexadecylamino)benzoyl chloride and 1.3 g. of triethylamine in 100 ml. ether is added 1.2 g. of piperidine. An immediate precipitate forms, the mixture is refluxed for one hour and then filtered. The solid is extracted several times with hot ether, and the ether is evaporated to yield a white solid. The solid is dissolved in tetrahydrofuran (100 ml.) and hydrogenated over 600 mg. 110% Pd-on-carbon at 50 psi. until hydrogen up-take stops. The catalyst is filtered and the filtrate evaporated. The residue is crystallized from acetic acid to yield N-[2-fluoro-4-(hexadecylamino)benzoyl]piperidine as a crystalline mass.

Workup

  1. temperatureAn immediate precipitate forms, the mixture is refluxed for one hour
  2. filtrationfiltered
  3. extractionThe solid is extracted several times with hot ether
  4. customthe ether is evaporated
  5. customto yield a white solid
  6. filtrationThe catalyst is filtered
  7. customthe filtrate evaporated
  8. customThe residue is crystallized from acetic acid

Sources & evidence

ORD record
ord-169ad9c5862743d38d81ece543231ee7
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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