Pyridine → HCID 18659963, compound

HRID 361592Notes

Reaction equation

HRID 361592 reaction equation
N1C=CC=CC=1.[N:7]1([CH2:12]/[CH:13]=[C:14](/[C:22]2[N:27]=[C:26](/[CH:28]=[CH:29]/[CH2:30][OH:31])[CH:25]=[CH:24][CH:23]=2)\[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1.[C:32](Cl)(=[O:34])[CH3:33]>C(Cl)Cl>[C:32]([O:31][CH2:30]/[CH:29]=[CH:28]/[C:26]1[CH:25]=[CH:24][CH:23]=[C:22](/[C:14](/[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:13]/[CH2:12][N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[N:27]=1)(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 18659962HCID 18659962, compound

Product 1

HCID 18659963HCID 18659963, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (110 μl, 1.36 mmol) was added to a solution of 3-(6-[3-pyrrolidino-1-{4-tolyl}-prop-1E-enyl]-pyridin-2-yl)-prop-2E-en-1-ol (227 mg, 0.68 mmol) in DCM (3 ml) under an inert atmosphere. Acetyl chloride (72 μl, 1.02 mmol) was added and the reaction stirred for 18 hours at room temperature. The reaction mixture was partitioned between DCM and brine. The organic layer was separated, dried over sodium sulphate, filtered and concentrated under vacuum to leave a brown oil. The product was purified by column chromatography on silica gel eluting with 5% methanol/DCM. Product containing fractions were combined and solvent removed to yield 3-(6-[3-pyrrolidino-1-{4-tolyl}-prop-1E-enyl]-pyridin-2-yl)-prop-2E-en-1-yl acetate as a brown gum (184 mg, 73%). 1H-NMR; δ (CDCl3), 7.49 (1H, t, J=7.8 Hz), 7.24 (2H, d, J=7.9 Hz), 7.18-7.11 (2H, m), 7.06 (2H, d, J=7.9 Hz), 6.91-6.66 (3H, m), 4.79 (2H, dd, J=5.4, 0.7 Hz), 3.72 (2H, m), 3.20 (4H, bm), 2.40 (3H, s), 2.12 (3H, s) and 2.11-2.02 (4H, m).

Workup

  1. customThe reaction mixture was partitioned between DCM and brine
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto leave a brown oil
  7. customThe product was purified by column chromatography on silica gel eluting with 5% methanol/DCM
  8. additionProduct containing fractions
  9. customsolvent removed

Sources & evidence

ORD record
ord-c5f55809686b45ad935b4b14cb522c24
Source dataset
uspto-grants-1999_02
Patent number
US05866588

Reaction notes

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