Ammonium formate → HCID 9920993, compound

HRID 1582447Notes

Reaction equation

HRID 1582447 reaction equation
C([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:13]2[CH2:20][CH2:21][N:22](CC3C=CC=CC=3)[CH2:23][CH2:24][C:12]=12)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH2:24]1[C:12]2=[C:11]([CH2:10][CH2:9][NH2:8])[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]2[CH2:20][CH2:21][NH:22][CH2:23]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 12147288HCID 12147288, compound

Product 1

HCID 9920993HCID 9920993, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-benzyl-2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanamine (195 mg, 0.48 mmol) in methanol (10 mL) is treated with 10% palladium on carbon (40 mg) and ammonium formate (210 mg, 3.3 mmol) followed by heating to reflux. After 18 hrs, the reaction is cooled to rt, filtered through celite, and concentrated to give a crude yellow oil. This material is purified by LC (230-400 silica gel) eluting with 20:2.5:77.5 methanol/ammonuim hydroxide/dichloromethane to afford 51 mg (47%) of 2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanamine as a colorless oil that solidified, mp 77-80° C. MS (EI) m/z 229 (M+); % Water (KF): 0.94; Anal. Calculated for C14H19N3.0.94 H2O: C, 72.64; H, 8.38; N, 18.15. Found: C, 72.66; H, 8.32; N, 18.03.

Workup

  1. temperatureby heating to reflux
  2. filtrationfiltered through celite
  3. concentrationconcentrated
  4. customto give a crude yellow oil
  5. customThis material is purified by LC (230-400 silica gel)
  6. washeluting with 20:2.5:77.5 methanol/ammonuim hydroxide/dichloromethane

Sources & evidence

ORD record
ord-7f9dfdccf6274f4288233007c0c8b76b
Source dataset
uspto-grants-2004_05
Patent number
US06734301B2

Reaction notes

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