Pyridine → HCID 12510296, compound

HRID 259355Notes

Reaction equation

HRID 259355 reaction equation
Cl.C[NH:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]23[CH2:20][CH:15]4[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]4)[CH2:12]2)[CH2:18]3)=[CH:6][CH:5]=1.N1C=CC=CC=1.Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29]>O>[C:28]([NH:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]23[CH2:12][CH:13]4[CH2:19][CH:17]([CH2:16][CH:15]([CH2:14]4)[CH2:20]2)[CH2:18]3)=[CH:8][CH:9]=1)([O:30][CH2:31][CH3:32])=[O:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 20342222HCID 20342222, compound

Product 1

HCID 12510296HCID 12510296, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the free base from 2.82 g. of the N-methyl-4-(1-adamantyloxy)aniline hydrochloride in 20 ml. pyridine was treated dropwise with 1.64 ml. ClCO2C2H5. Following 18 hours standing in the cold the mixture was pured into ice: H2O. This was extracted with Et2O and the organic layer washed in turn with H2O, cold 2.5 N HCl, H2O NaHCO3 and brine. The extract was then taken to dryness to leave behind N-methyl, N-carbethoxy-4-(1-adamantyloxy)aniline as an oil.

Workup

  1. extractionThis was extracted with Et2O
  2. washthe organic layer washed in turn with H2O, cold 2.5 N HCl, H2O NaHCO3 and brine

Sources & evidence

ORD record
ord-598608771fa8478188d58d3c7d0124ff
Source dataset
uspto-grants-1977_07
Patent number
US04036977

Reaction notes

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