Methyl iodide → N,N-dibenzyl-2-(1-methoxycyclopropyl)ethanamine

HRID 715117Notes

Reaction equation

HRID 715117 reaction equation
[CH2:1]([N:8]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:9][CH2:10][C:11]1([OH:14])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:25]>C1COCC1>[CH2:15]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:9][CH2:10][C:11]1([O:14][CH3:25])[CH2:12][CH2:13]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 574578281-[2-(Dibenzylamino)ethyl]cyclopropanol

Product 1

HCID 89814525N,N-dibenzyl-2-(1-methoxycyclopropyl)ethanamineYield 38.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Treat a 0° C. solution of 1-(2-(dibenzylamino)ethyl)cyclopropanol (3 g, 10.6 mmol) in THF (50 mL), under N2, portion wise with NaH (60%, 0.85 g, 21.3 mmol), stir at 0° C. for 0.5 h, add iodomethane (1.82 g, 12.8 mmol) drop wise, warm to RT and stir for 3 h. Cool the mixture to 0° C., quench with satd. NH4Cl and partially concentrate. Extract with EtOAc (3×), wash the combined organics with brine, dry over Na2SO4, concentrate and purify via silica gel chromatography to afford the title compound (1.2 g, 38%). 1H NMR (400 MHz, CDCl3): δ 7.39-7.21 (m, 10H), 3.60 (s, 4H), 3.12 (s, 3H), 2.65 (t, J=8 Hz, 2H), 1.75 (t, J=8 Hz, 2H), 0.68-0.65 (m, 2H), 0.34-0.31 (m, 2H).

Workup

  1. temperatureCool the mixture to 0° C.
  2. customquench with satd
  3. concentrationNH4Cl and partially concentrate
  4. extractionExtract with EtOAc (3×)
  5. washwash the combined organics with brine
  6. dry with materialdry over Na2SO4
  7. concentrationconcentrate
  8. custompurify via silica gel chromatography

Sources & evidence

ORD record
ord-7a79aae221144424b6a039e125ebd91f
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

Loading…