Pivaloyl chloride → 3-{N-[beta-(3,4-Dipivalyloxyphenyl)ethyl]}carbamoylpyridine

HRID 1633218Notes

Reaction equation

HRID 1633218 reaction equation
[C:1]([NH:9][CH2:10][CH2:11][C:12]1[CH:19]=[CH:18][C:16]([OH:17])=[C:14]([OH:15])[CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH3:20][C:21]([CH3:26])([CH3:25])[C:22](Cl)=[O:23]>C(Cl)(Cl)Cl>[C:22]([O:15][C:14]1[CH:13]=[C:12]([CH2:11][CH2:10][NH:9][C:1]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)=[O:8])[CH:19]=[CH:18][C:16]=1[O:17][C:22](=[O:23])[C:21]([CH3:26])([CH3:25])[CH3:20])(=[O:23])[C:21]([CH3:26])([CH3:25])[CH3:20]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 13473418N-nicotinoyl dopamine

Product 1

HCID 134734203-{N-[beta-(3,4-Dipivalyloxyphenyl)ethyl]}carbamoylpyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 5.16 g (0.02 mol) finely powdered nicotinoyldopamine in 100 ml of chloroform, 7.23 g (0.06 mol) trimethylacetyl chloride was dropped while stirring. The mixture was refluxed for 6 hrs and then filtered. The filtrate was washed with water until free of chloride ions, then washed once with 5% solution of NaHCO3 then with water. Chloroform was distilled off on rotavap and the residue was chromatographed using silica gel G column and 2% methanol in chloroform as the elution solvent. The first fraction was collected, evaporated and the residue was crystallized from ether/pet. ether. Yield 6.2 g (78%) of white crystalline solid, m.p. 112°-114° C., PMR (CDCl3) 9.06 (bs, 1H, C2 pyridine proton), 8.73 (bd, 1H, C6 pyridine proton), 8.30-8.13 (m, 1H, C4 pyridine proton), 7.46-7.10 (m, 5H, C6H3 +C5 pyridine proton+CONH), 3.66 (q, 2H, J=6.25 Hz, ##STR35## 3.0 (t, 2H, J=6.5 Hz, --CH2), 1.41 (s, 18H, 2--C--(CH3)3). Anal. (C24H30N2O5) C, H, N.

Workup

  1. additionwas dropped
  2. temperatureThe mixture was refluxed for 6 hrs
  3. filtrationfiltered
  4. washThe filtrate was washed with water until free of chloride ions
  5. washwashed once with 5% solution of NaHCO3
  6. distillationChloroform was distilled off on rotavap
  7. customthe residue was chromatographed
  8. customThe first fraction was collected
  9. customevaporated
  10. customthe residue was crystallized from ether/pet. ether

Sources & evidence

ORD record
ord-23ec53e787b04f6f802b1f557ca4900e
Source dataset
uspto-grants-1984_10
Patent number
US04479932

Reaction notes

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