Triethylamine → HCID 22662758, compound

HRID 392073Notes

Reaction equation

HRID 392073 reaction equation
Cl[CH:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[CH2:3][CH3:4].[NH2:13][C:14]1[C:29]([Cl:30])=[CH:28][C:17]([C:18]([O:20][CH2:21][CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[O:19])=[C:16]([O:31][CH3:32])[CH:15]=1.C(N(CC)CC)C>CN(C=O)C>[NH2:13][C:14]1[C:29]([Cl:30])=[CH:28][C:17]([C:18]([O:20][CH2:21][CH:22]2[CH2:23][CH2:24][N:25]([CH2:4][CH2:3][CH2:2][O:5][C:6]3[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=3)[CH2:26][CH2:27]2)=[O:19])=[C:16]([O:31][CH3:32])[CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22662739HCID 22662739, compoundHCID 226627574-Piperidinylmethyl 4-amino-5-chloro-2-methoxybenzoate

Product 1

HCID 22662758HCID 22662758, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-chloro-(4-fluorophenoxy)propane (2.3 g), intermediate 11 (3 g) and N,N-diethylethanamine (2.8 ml) in DMF (50 ml) was stirred for 48 hours at 70° C. The reaction mixture was cooled and the solvent was evaporated. The residue was partitioned between DCM and water. The organic layer was separated, washed with water, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from ACN (0° C.). The precipitate was filtered off and dried (vacuum; 50° C.), yielding 1.17 g (26%) [1-[3-(4-fluorophenoxy)propyl]-4-piperidinyl]methyl 4-amino-5-chloro-2-methoxybenzoate (compound 1, mp. 140.0° C.).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent was evaporated
  3. customThe residue was partitioned between DCM and water
  4. customThe organic layer was separated
  5. washwashed with water
  6. customdried
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated
  12. customThe residue was crystallized from ACN (0° C.)
  13. filtrationThe precipitate was filtered off
  14. customdried (vacuum; 50° C.)

Sources & evidence

ORD record
ord-a1f4f59beea84b7a9e6172d00909172b
Source dataset
uspto-grants-2004_10
Patent number
US06800628B2

Reaction notes

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