Guanidine → HCID 178455162, compound

HRID 1109633Notes

Reaction equation

HRID 1109633 reaction equation
[NH2:1][C:2]([NH2:4])=[NH:3].CO[C:7]1[CH:12]([C:13](OCC)=[O:14])[CH2:11][CH:10]([CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:9][N:8]=1>O>[NH2:3][C:2]1[N:4]=[C:13]([OH:14])[C:12]2[CH2:11][CH:10]([CH2:18][O:19][Si:20]([C:23]([CH3:25])([CH3:24])[CH3:26])([CH3:22])[CH3:21])[CH2:9][NH:8][C:7]=2[N:1]=1

Participants

4

Reactant 2

HCID 3520GuanidineHCID 15386083HCID 15386083, compound

Product 1

HCID 178455162HCID 178455162, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 9.8 g of guanidine free base and 13.8 g of 2-methoxy-3-carboethoxy-5-[t-butyl(dimethyl)silyloxymethyl]-3,4,5,6-tetrahydropyridine was heated at 90° C. under nitrogen for 18 hours. The mixture was cooled to room temperature, and water was added to give a white precipitate. This was filtered to give 9.5 g of the title compound: MS m/z 311 (M+ +1), 310 (M+); 300-MHz 1H NMR (DMSO-d6) δ0.03 (s, 6H), 0.85 (s, 9H), 1.70-1.88 (m, 2H), 2.27-2.38 (m, 1H), 2.78-2.88 (m, 1H), 3.16-3.27 (m, 1H), 3.37-3.45 (m, 1H), 3.49-3.58 (m, 1H), 5.92 (b s, 2H), 6.21 (b s, 1H), 9.67 (b s, 1H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customto give a white precipitate
  3. filtrationThis was filtered

Sources & evidence

ORD record
ord-7570a4157c5148b785696c9ce7467c40
Source dataset
uspto-grants-1994_06
Patent number
US05321150

Reaction notes

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