Pyridine → [(cis)-1-Acetyl-6-bromo-2-propyl-1,2,3,4-tetrahydro-4-quinolinyl]formamide

HRID 2041719Notes

Reaction equation

HRID 2041719 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C@@H:7]([CH2:12][CH2:13][CH3:14])[CH2:6][C@H:5]2[NH:15][CH:16]=[O:17].[C:18](Cl)(=[O:20])[CH3:19].N1C=CC=CC=1>C(Cl)Cl>[C:18]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2)[C@H:5]([NH:15][CH:16]=[O:17])[CH2:6][C@@H:7]1[CH2:12][CH2:13][CH3:14])(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 86669448[(cis)-6-Bromo-2-propyl-1,2,3,4-tetrahydro-4-quinolinyl]formamide

Product 1

HCID 86669447[(cis)-1-Acetyl-6-bromo-2-propyl-1,2,3,4-tetrahydro-4-quinolinyl]formamideYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

[(cis)-6-Bromo-2-propyl-1,2,3,4-tetrahydro-4-quinolinyl]formamide (for a preparation see intermediate 89) (8.0 g, 26.9 mmol) in DCM (100 mL) was added dropwise at room temperature to a mixture of acetyl chloride (6.7 mL, 94.28 mmol) and pyridine (10.85 mL, 134.7 mmol) in DCM (150 mL). The resulting mixture was stirred at this temperature for 1 h then was washed with 1M NaOH aqueous solution, 1M HCl aqueous solution, a saturated NaHCO3 aqueous solution then brine, was dried over MgSO4 and concentrated in vacuovacuo. Purification of the residue by flash chromatography on silica gel (20:1 DCM/MeOH) gave [(cis)-1-acetyl-6-bromo-2-propyl-1,2,3,4-tetrahydro-4-quinolinyl]formamide (6.29 g, 18.5 mmol, 68%) as a light orange solid.

Workup

  1. washthen was washed with 1M NaOH aqueous solution, 1M HCl aqueous solution
  2. dry with materiala saturated NaHCO3 aqueous solution then brine, was dried over MgSO4
  3. concentrationconcentrated in vacuovacuo
  4. customPurification of the residue by flash chromatography on silica gel (20:1 DCM/MeOH)

Sources & evidence

ORD record
ord-c53f52c985634eee9c41dc773763c218
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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