Ammonium formate → Ammonium Hydroxide

HRID 1901556Notes

Reaction equation

HRID 1901556 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 slution 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

Sources & evidence

ORD record
ord-25f1bc9e0804474882b9bd8e13cb0d0b
Source dataset
uspto-grants-1996_11
Patent number
US05578612

Reaction notes

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