Sodium Hydroxide → HCID 22941954, compound

HRID 361594Notes

Reaction equation

HRID 361594 reaction equation
[N:1]1([CH2:6]/[CH:7]=[C:8](/[C:16]2[N:21]=[C:20](/[CH:22]=[CH:23]/[CH2:24][N:25]=[N+]=[N-])[CH:19]=[CH:18][CH:17]=2)\[C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Sn](Cl)Cl.[OH-].[Na+]>CO>[N:1]1([CH2:6]/[CH:7]=[C:8](/[C:16]2[N:21]=[C:20](/[CH:22]=[CH:23]/[CH2:24][NH2:25])[CH:19]=[CH:18][CH:17]=2)\[C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 22941955HCID 22941955, compound

Product 1

HCID 22941954HCID 22941954, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of {3-(6-[3-pyrrolidino-1-{4-tolyl}-prop-1E-enyl]-pyridin-2-yl)-prop-2E-enyl}-azide (154 mg, 0.43 mmol) in methanol (10 ml) was treated with tin (II) chloride (163 mg, 0.86 mmol). The reaction showed a slight exotherm and darkened in colour. After 1 hour solvent was removed under reduced pressure to leave a green gum. The residue was treated with sodium hydroxide solution (5M) and the product extracted (×4) with diethyl ether. The combined organic extracts were combined, dried over magnesium sulphate, filtered and solvent removed to yield {3-(6-[3-pyrrolidino-1-{4-tolyl}-prop-1E-enyl]-pyridin-2-yl)-prop-2E-enyl}-amine as a brown gum (77.5 mg, 54%). 1H-NMR; δ (CDCl3), 7.43 (1H, t, J=8.1 Hz), 7.21 (3H, m), 7.09 (3H, m), 6.99 (1H, dt, J=16.3, 6.3 Hz), 6.69 (1H, d, J=8.0 Hz), 6.61 (1H, dt, J=15.6, 1.4 Hz), 3.56 (2H, dd, J=5.8, 1.3 Hz), 3.21 (2H, d, J=9.6 Hz), 2.56 (4H, m), 2.40 (3H, s), 1.79 (4H, s) and 1.71 (2H, bs).

Workup

  1. customAfter 1 hour solvent was removed under reduced pressure
  2. customto leave a green gum
  3. extractionthe product extracted (×4) with diethyl ether
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customsolvent removed

Sources & evidence

ORD record
ord-56bc3987362844ba96af773bd5c75b91
Source dataset
uspto-grants-1999_02
Patent number
US05866588

Reaction notes

Loading…