Triethylamine → HCID 21182325, compound

HRID 1872363Notes

Reaction equation

HRID 1872363 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]([OH:21])=O)[CH:13]=[CH:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].S(Cl)(Cl)=[O:23].C([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])C.[CH2:33]([O:40][C:41]1[CH:42]=C2C(=CC=1)C=C(C(Cl)=O)C=C2)[CH2:34]CCCCC>ClCCl>[CH2:33]([O:40][C:41]([CH:42]1[CH2:30][CH2:29][N:28]([C:19]([C:14]2[CH:13]=[CH:12][C:11]3[C:16](=[CH:17][CH:18]=[C:9]([O:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH:10]=3)[CH:15]=2)=[O:21])[CH2:31][CH2:32]1)=[O:23])[CH3:34]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 10731954HCID 10731954, compoundHCID 21182412HCID 21182412, compound

Product 1

HCID 21182325HCID 21182325, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 6-Heptyloxynaphthalen-2-carboxylic acid (1.00 g) and thionyl chloride (5 ml) was stirredn for 18 hours at ambient temparature, and concentrated under reduced pressure to give crude 6-hepthyloxy-2-naphthoyl chloride. To a mixture of ethyl isonipecotinate (605 mg), triethylamine (425 mg) and N,N-dimethylaminopyridine (10 mg) in dichloromethane (10 ml) was added crude 6-heptyloxy-2-naphthoyl chloride, and the mixture was stirred for 2 hours at ambient temperature, and diluted with dichloromethane. The mixture was washed with water, 1N hydrochloric acid and brine, and dried over magnesium sulfate. The magnesium sulfate was filtered off, and filtrate was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel, and eluted with (n-hexane:ethyl acetate=3:1) to give 4-Ethoxycarbonyl-1-(6-heptyloxy-2-naphthoyl)piperidine (1.20 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give crude 6-hepthyloxy-2-naphthoyl chloride
  3. additionTo a mixture of ethyl
  4. washThe mixture was washed with water, 1N hydrochloric acid and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe magnesium sulfate was filtered off
  7. customfiltrate was evaporated under reduced pressure
  8. washeluted with (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-f8e62a1fa0c94aa7b92ad3f70a4f26d6
Source dataset
uspto-grants-2000_08
Patent number
US06107458

Reaction notes

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