Hydrochloric Acid → 2-[[2-(3-Butoxy-phenyl)-ethyl]-(tetrahydrofuran-3-ylmethyl)amino]-N,N-dimethyl-acetamide hydrochloride

HRID 2264666Notes

Reaction equation

HRID 2264666 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][N:10]([CH2:17][CH:18]2[CH2:22][CH2:21][O:20][CH2:19]2)[CH2:11][C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[CH:5]=[CH:6][CH:7]=1.Br[CH2:24][CH2:25][CH2:26][CH3:27].C(=O)([O-])[O-].[K+].[K+].[I].[K].[ClH:36]>CN(C=O)C.CCOC(C)=O.C(OCC)C>[ClH:36].[CH2:24]([O:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][N:10]([CH2:17][CH:18]2[CH2:22][CH2:21][O:20][CH2:19]2)[CH2:11][C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[CH:5]=[CH:6][CH:7]=1)[CH2:25][CH2:26][CH3:27]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 595968312-[[2-(3-hydroxy-phenyl)-ethyl]-(tetrahydrofuran-3-ylmethyl)amino]-N,N-dimethyl-acetamideHCID 178506587HCID 178506587, compound

Product 1

HCID 665912022-[[2-(3-Butoxy-phenyl)-ethyl]-(tetrahydrofuran-3-ylmethyl)amino]-N,N-dimethyl-acetamide hydrochlorideYield 50%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-[[2-(3-hydroxy-phenyl)-ethyl]-(tetrahydrofuran-3-ylmethyl)amino]-N,N-dimethyl-acetamide (1.0 g 3.3 mmol), 1-bromobutane (0.43 ml, 4 mmol), potassium carbonate (680 mg 5 mmol), potassium iodine (50 mg, 0.3 mmol), in DMF (30 ml) was refluxed for 16 h. After filtration over celite pad, the solution was evaporated from the solvent and the crude oil obtained purified by preparative HPLC. The hydrochloride salt was prepared by adding HCl 1N in AcOEt to the free amine dissolved in ethyl ether. After filtration, 690 mg (50% yield) the title compound was obtained as a white solid of 99% purity.

Workup

  1. filtrationAfter filtration over celite pad
  2. customthe solution was evaporated from the solvent
  3. customthe crude oil obtained
  4. custompurified by preparative HPLC
  5. filtrationAfter filtration

Sources & evidence

ORD record
ord-8885e7c0d9a8486eac642bb50d8f14f1
Source dataset
uspto-grants-2010_12
Patent number
US07855227B2

Reaction notes

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