Ammonium formate → Ammonium Hydroxide

HRID 744138Notes

Reaction equation

HRID 744138 reaction equation
C([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)=O)C1C=CC=CC=1.C(OC([N:36]1[CH2:41][CH2:40][CH2:39]C[CH:37]1[CH2:42][C:43]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[NH:45][CH:44]=1)=O)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[OH-:8].[NH4+:11].[NH:36]1[CH2:41][CH2:40][CH2:39][CH:37]1[CH2:42][C:43]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[NH:45][CH:44]=1.[NH:11]1[CH2:9][CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1

Participants

8

Reactant 3

HCID 2723923Ammonium formateHCID 120500533-(N-benzyloxycarbonylpyrrolidin-2-ylmethyl)-1H-indoleHCID 199702443-(N-benzyloxycarbonylpiperid-2-ylmethyl)-1H-indole

Product 3

HCID 14923Ammonium HydroxideHCID 21346Indole, 3-(2-piperidylmethyl)-HCID 185089963-(pyrrolidin-2-ylmethyl)-1H-indole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the 3-(N-benzyloxycarbonylpyrrolidin-2-ylmethyl)-1H-indole or the 3-(N-benzyloxycarbonylpiperid-2-ylmethyl)-1H-indole (2.00 mmol), 10% palladium on carbon (0.20 g), and ammonium formate (1.26 g, 20 mmol, 10 eq) in absolute ethanol (15 mL) was stirred under a nitrogen atmosphere for 4 hours. The resulting reaction mixture was filtered through diatomaceous earth, and the filtrate was evaporated under reduced pressure. The residue was column chromatographed using silica gel (approximately 50 g) and elution with a solution of methylene chloride: methanol:ammonium hydroxide [8:2:0.2] or other appropriate solvent system to afford the corresponding 3-(pyrrolidin-2-ylmethyl)-1H-indole or 3-(piperid-2-ylmethyl)-1H-indole.

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas filtered through diatomaceous earth
  3. customthe filtrate was evaporated under reduced pressure
  4. customchromatographed
  5. washsilica gel (approximately 50 g) and elution with a solution of methylene chloride

Sources & evidence

ORD record
ord-00937b672b454cf3a774b1da363078f1
Source dataset
uspto-grants-1996_09
Patent number
US05559129

Reaction notes

Loading…