Ammonium formate → Ammonium Hydroxide

HRID 1077851Notes

Reaction equation

HRID 1077851 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-cc6a72720f934046a09da63877e975bb
Source dataset
uspto-grants-1996_08
Patent number
US05545644

Reaction notes

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