Methanol → HCID 571497, compound

HRID 749056Notes

Reaction equation

HRID 749056 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:20]2OC3[C:13](=CC=CC=3)[NH:12][C:11]=2C=C[CH:8]=1.NCCC1CCCN1C.[Cl-].[Al+3].[Cl-].[Cl-].CO>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:8][N:12]([CH3:13])[CH2:11][CH2:20]1

Participants

6

Reactant 4

HCID 887MethanolHCID 983882-(2-Aminoethyl)-1-methylpyrrolidineHCID 6451240Aluminum(III) ChlorideHCID 68902061HCID 68902061, compound

Product 1

HCID 571497HCID 571497, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Pyridinyl phenoxazine (13 mg, 0.1181 mmol), 2-(2-aminoethyl)-1-methylpyrrolidine (22 ul, 0.1518 mmol) and aluminum chloride (27 mg, 0.2025 mmol) were mixed in anhydrous dichloromethane (1 ml) and stirred for 1 h. The mixture was then evaporated to a residue which was washed with saturated aqueous sodium potassium tartaric acid. The mixture was then extracted with 3×10 ml dichloromethane and the extracts dried (Na2SO4) and evaporated. The compound was then isolated using preparative thin layer chromatography (Al2O3, 3% MeOH in dichloromethane) to yield the 4-pyridinyl methylpyrrolidine (11 mg) as a yellow solid.

Workup

  1. customThe mixture was then evaporated to a residue which
  2. washwas washed with saturated aqueous sodium potassium tartaric acid
  3. extractionThe mixture was then extracted with 3×10 ml dichloromethane
  4. dry with materialthe extracts dried (Na2SO4)
  5. customevaporated
  6. customThe compound was then isolated

Sources & evidence

ORD record
ord-2a043f259fef4fa196d639aedc910b82
Source dataset
uspto-grants-2008_07
Patent number
US07402579B2

Reaction notes

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