HCID 21217923, compound → HCID 21217870, compound

HRID 1586235Notes

Reaction equation

HRID 1586235 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=2)[CH2:10][CH2:11][CH2:12][OH:13])[CH:6]=[CH:7][CH:8]=1)#[N:2].[H][H]>CO.[OH-].[OH-].[Pd+2]>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([N:9]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=2)[CH2:10][CH2:11][CH2:12][OH:13])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 21217923HCID 21217923, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21217870HCID 21217870, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Part E. 3-[[3-cyanophenyl][4-(4-nitrophenyl)butyl]amino]-1-propanol (1.4 gm, 3.96 mmol) was dissolved in 25 mL of methanol, followed by the addition of 0.14 gm of 20% Pd(OH)2 /C and placed under a balloon of hydrogen for 2.5 hours. The resulting solution was filtered through a pad of celite and the volatiles removed under vacuum to give the title compound as a clear semi-solid 1.30 gm, (100%) MS m/e 328.3 (M+H)+ 1 H NMR (CD3OD) 1.60 (br s, 4H), 1.78 (m, 2H), 2.54 (br s, 2H), 3.32 (s, 2H), 3.42 (t, 2H), 3.62 (t, 2H), 3.99 (s, 2H), 6.71-6.62 (m, 5 H), 6.93 (d, 2H), 7.20 (t, 1H).

Workup

  1. filtrationThe resulting solution was filtered through a pad of celite
  2. customthe volatiles removed under vacuum

Sources & evidence

ORD record
ord-413564b5f85e46f385026cd28df0174a
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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