Methanol → (4-Pyrrolidin-1-yl-cyclohexyl)-methylamine

HRID 1819480Notes

Reaction equation

HRID 1819480 reaction equation
C(OC(=O)NC[CH:12]1[CH2:17][CH2:16][CH:15]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:14][CH2:13]1)C1C=CC=CC=1.C([O-])=O.[NH4+:27].[CH3:28]O>>[N:18]1([CH:15]2[CH2:14][CH2:13][CH:12]([NH:27][CH3:28])[CH2:17][CH2:16]2)[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

4

Reactant 3

HCID 887MethanolHCID 2723923Ammonium formateHCID 69058995(4-Pyrrolidin-1-yl-cyclohexylmethyl)-carbamic acid benzyl ester

Product 1

HCID 57457676(4-Pyrrolidin-1-yl-cyclohexyl)-methylamine

Conditions

Temperature
65 °C

Procedure

To a solution of (4-pyrrolidin-1-yl-cyclohexylmethyl)-carbamic acid benzyl ester (292 mg, 0.92 mmol) in MeOH (5 mL) was added ammonium formate (0.58 g, 9.20 mmol). The reaction flask was flushed with N2 prior to addition of 10% Pd/C (300 mg). The mixture was heated at 65° C. for 2 h whereupon TLC analysis (silica gel, 95:4.75:0.25 DCM/MeOH/NH4OH) showed complete consumption of 57. After cooling to room temperature the reaction mixture was filtered through a plug of celite in order to remove the Pd catalyst. The filtrate contained (4-pyrrolidin-1-yl-cyclohexyl)-methylamine which was used without further purification in the next step.

Workup

  1. customThe reaction flask was flushed with N2
  2. additionto addition of 10% Pd/C (300 mg)
  3. customconsumption of 57
  4. temperatureAfter cooling to room temperature the reaction mixture
  5. filtrationwas filtered through a plug of celite in order
  6. customto remove the Pd catalyst
  7. customwas used without further purification in the next step

Sources & evidence

ORD record
ord-2fd31955a9b340e9906b9b2d6467a35c
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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