Diisopropylethylamine → Methyl 4-(piperidin-4-yl)-1-naphthoate

HRID 352360Notes

Reaction equation

HRID 352360 reaction equation
C[N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]([O:20][CH3:21])=[O:19])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.C(N(C(C)C)C(C)C)C.ClC(OC(Cl)C)=O>C(Cl)Cl>[NH:2]1[CH2:3][CH2:4][CH:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]([O:20][CH3:21])=[O:19])=[CH:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformateHCID 22711881Methyl 4-(1-methylpiperidin-4-yl)-1-naphthoate

Product 1

HCID 22711878Methyl 4-(piperidin-4-yl)-1-naphthoateYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of D9 (0.39 g, 1.4 mmole) in DCM (30 ml) was treated with iPr2EtN (0.26 g, 2 mmole) followed by 1-chloroethyl chloroformate (0.29 g, 2 mmole) and stirred at room temperature for 3 h, then concentrated under vacuum and the residue treated with MeOH (30 ml) and heated under reflux for 1 h. The mixture was allowed to cool and the solid filtered off, washed with Et2O and dried. This was treated with 10% Na2CO3 solution, extracted with DCM and the extract dried and concentrated under vacuum to afford the title compound as a colourless oil (0.33 g, 88%).

Workup

  1. concentrationconcentrated under vacuum
  2. additionthe residue treated with MeOH (30 ml)
  3. temperatureheated
  4. temperatureunder reflux for 1 h
  5. temperatureto cool
  6. filtrationthe solid filtered off
  7. washwashed with Et2O
  8. customdried
  9. additionThis was treated with 10% Na2CO3 solution
  10. extractionextracted with DCM
  11. customthe extract dried
  12. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b50637576bef4526889503b437468e8b
Source dataset
uspto-grants-2004_06
Patent number
US06747030B1

Reaction notes

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