Ammonium formate → 3-Methyl-3,9-diazabicyclo[4.2.1]nonane

HRID 1986015Notes

Reaction equation

HRID 1986015 reaction equation
C([O-])=O.[NH4+].C([N:12]1[CH:18]2[CH2:19][CH2:20][CH:13]1[CH2:14][N:15]([CH3:21])[CH2:16][CH2:17]2)C1C=CC=CC=1>[Pd].C(O)C>[CH3:21][N:15]1[CH2:16][CH2:17][CH:18]2[NH:12][CH:13]([CH2:20][CH2:19]2)[CH2:14]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 688447863-Methyl-9-(phenylmethyl)-3,9-diazabicyclo[4.2.1]nonane

Product 1

HCID 199082313-Methyl-3,9-diazabicyclo[4.2.1]nonane

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Neat ammonium formate (2 g, 31.7 mmol) was added to stirred suspension of 9-benzyl-3-methyl-3,9-diazabicyclo[4.2.1]nonane (250 mg, 1.085 mmol) and 10% Pd-C (150 mg, 0.141 mmol) in abs. ethanol (50 ml). The mixture was heated to reflux for 2-3 h. The suspension was filtered and to the filtrate TFA (0.5 ml) was added and evaporated to dryness to afford 3-methyl-3,9-diazabicyclo[4.2.1]nonane and isolated as the bis-TFA salt. LC/MS: m/e 141 (MH+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2-3 h
  3. filtrationThe suspension was filtered and to the filtrate TFA (0.5 ml)
  4. additionwas added
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-3a1eb98057c141faaea31e25e1f5c41c
Source dataset
uspto-grants-2009_06
Patent number
US07547690B2

Reaction notes

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