2-(Dimethylamino)ethanol → HCID 67740218, compound

HRID 580991Notes

Reaction equation

HRID 580991 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[CH:7]=[CH:6][C:5]=1[C:14]#[C:15][C:16]1([OH:24])[CH:21]2[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]2)[CH2:17]1)[CH:2]=[CH2:3].[C-]#N.[Na+].[CH3:28][N:29]([CH3:33])[CH2:30]CO>>[CH2:1]([C:4]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH2:28][N:29]([CH3:33])[CH3:30])=[O:11])[CH:7]=[CH:6][C:5]=1[C:14]#[C:15][C:16]1([OH:24])[CH:21]2[CH2:20][CH2:19][N:18]([CH2:23][CH2:22]2)[CH2:17]1)[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 8929Sodium CyanideHCID 53889607HCID 53889607, compound

Product 1

HCID 67740218HCID 67740218, compound

Conditions

Temperature
90 °C

Procedure

A mixture of 3-[2-(2-allyl-4-methoxycarbonylphenyl)ethynyl]quinuclidin-3-ol (0.64 g), sodium cyanide (50 mg) and N,N-dimethylethanolamine (10 ml) was heated at 90° C. for 24 hours. The mixture was evaporated to give an oil which was partitioned between ethyl acetate and water. The organic phase was separated, washed with brine, dried (MgSO4) and evaporated. The residue was purified by flash column chromatography on silica gel using 10% methanol in dichloromethane containing 1% ammonia (density 0.88 g/cm3) as eluent to give 3-[2-(2-allyl-4-(2-(N,N-dimethylamino)ethoxycarbonyl)phenyl)ethynyl]quinuclidin-3-ol as a gum (0.559 g); microanalysis found: C, 66.7; H, 7.6; N, 6.7%, C23H30N2O3.0.4CH2Cl2.0.1 H2O requires 7.47; N, 6.7%; NMR (CDCl3): 1.32-1.55(1H, m), 1.55-1.88(1H, m), 1.88-2.20(3H, m), 2.33(6H, s), 2.70(2H, t), 2.65-3.15(4H, m), 3.07(1H, d), 3.33(1H, dd), 3.56(2H, d), 4.41(2H, t), 4.98-5.15(2H, m), 5.29(CH2Cl2), 5.85-6.10(1H, m), 7.43(1H, d) and 7.71-7.90(2H, m); m/Z 383 (M+H).

Workup

  1. customThe mixture was evaporated
  2. customto give an oil which
  3. customwas partitioned between ethyl acetate and water
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by flash column chromatography on silica gel using 10% methanol in dichloromethane containing 1% ammonia (density 0.88 g/cm3) as eluent

Sources & evidence

ORD record
ord-662123edce2c4031ac2cc6db090b3e34
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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