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

HRID 2081989Notes

Reaction equation

HRID 2081989 reaction equation
[C:1]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH3:19][C:20]([CH3:25])([CH3:24])[C:21](Cl)=[O:22]>C(Cl)(Cl)Cl>[C:21]([O:18][C:15]1[CH:14]=[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:17][CH:16]=1)(=[O:22])[C:20]([CH3:25])([CH3:24])[CH3:19]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 3043417N-Nicotinoyl tyramine

Product 1

HCID 134734273-{N-[beta-(4-pivalyloxyphenyl)ethyl]}carbamoylpyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To an ice cold suspension of 4.84 g (0.02 mol) N-nicotinoyltyramine in 100 ml chloroform, 3.6 g (0.03 mol) of trimethylacetyl chloride were dropped while stirring. The mixture was refluxed overnight and the non-reacted nicotinoyltyramine was filtered off. The filtrate was washed once with 5% solution of NaHCO3 and then with water. Chloroform was evaporated on rotavap and the residue was crystallized from ether/pet. ether. Yield 3.9 g (60%), m.p. 80°-82° C. PMR (CDCl3 ) δ 8.66-6.93 (m, 8H, C5H4N+C6H4), 3.56 (q, 2H, J=7 Hz, ##STR1547## 2.86 (5, 2H, J=7 Hz, CH2), 1.33 (s, 9H, C--(CH3)3).

Workup

  1. additionwere dropped
  2. temperatureThe mixture was refluxed overnight
  3. filtrationthe non-reacted nicotinoyltyramine was filtered off
  4. washThe filtrate was washed once with 5% solution of NaHCO3
  5. customChloroform was evaporated on rotavap
  6. customthe residue was crystallized from ether/pet. ether

Sources & evidence

ORD record
ord-a8c8421a32fc45c18d8ee3d14dfabe37
Source dataset
uspto-grants-1993_02
Patent number
US05187158

Reaction notes

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