Methyl iodide → 3-Methyl-9-(phenylmethyl)-3,9-diazabicyclo[4.2.1]nonane

HRID 1986014Notes

Reaction equation

HRID 1986014 reaction equation
I[CH3:2].[CH2:3]([N:10]1[CH:16]2[CH2:17][CH2:18][CH:11]1[CH2:12][NH:13][CH2:14][CH2:15]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C1COCC1.CCOCC>[CH2:3]([N:10]1[CH:16]2[CH2:17][CH2:18][CH:11]1[CH2:12][N:13]([CH3:2])[CH2:14][CH2:15]2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 220579069-(phenylmethyl)-3,9-Diazabicyclo[4.2.1]nonane

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Neat Iodomethane (0.173 ml, 2.77 mmol) was added dropwise to a stirred solution of 9-benzyl-3,9-diazabicyclo[4.2.1]nonane (0.4 g, 1.849 mmol) and TEA (2.58 ml, 18.49 mmol) in THF (5 ml). The resultant suspension was stirred at rt for 3 hrs and diluted with ether and then filtered. The filtrate was evaporated to dryness to afford 9-benzyl-3-methyl-3,9-diazabicyclo[4.2.1]nonane as a light yellow oil. LC/MS: m/e 231 (MH+).

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-2bcccf325b2248d48cfe0c468388da44
Source dataset
uspto-grants-2009_06
Patent number
US07547690B2

Reaction notes

Loading…