Benzoyl chloride → HCID 54167160, compound

HRID 893023Notes

Reaction equation

HRID 893023 reaction equation
[CH3:1][C:2]1([CH2:16][N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH2:7][CH2:6][C:5]2[C:8]([CH3:15])=[C:9]([OH:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:4]=2[O:3]1.C(N(CC)CC)C.[C:30](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl>[C:30]([N:20]1[CH2:21][CH2:22][N:17]([CH2:16][C:2]2([CH3:1])[CH2:7][CH2:6][C:5]3[C:8]([CH3:15])=[C:9]([OH:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:4]=3[O:3]2)[CH2:18][CH2:19]1)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 10447779HCID 10447779, compound

Product 1

HCID 54167160HCID 54167160, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To stirred solution of 3,4-dihydro-2,5,7,8-tetramethyl-2-(1-piperazinylmethyl)-2H-1-benzopyran-6-ol (EXAMPLE 126, 0.3 g, 1.0 mmol), triethylamine (0.11 g, 1.1 mmol) and methylene chloride (3 ml) is added dropwise over 1-2 min a solution of benzoyl chloride (0.16 g, 1.1 mmol) in methylene chloride (2 ml). The mixture is stirred at 20°-25° for 1 hr and diluted with methylene chloride (20 ml), washed with water (20 ml), dried over sodium sulfate and the solvent removed at reduced pressure to leave a residue. The residue is flashed chromatographed on silica gel (25 g) eluting with ethyl acetate/hexane (1/1) to give the product as an oil that is crystallized from ether to give the title compound.

Workup

  1. washwashed with water (20 ml)
  2. dry with materialdried over sodium sulfate
  3. customthe solvent removed at reduced pressure
  4. customto leave a residue
  5. customThe residue is flashed chromatographed on silica gel (25 g)
  6. washeluting with ethyl acetate/hexane (1/1)

Sources & evidence

ORD record
ord-6e8eab69cf2e4ae6b39ef6a8bae4a53a
Source dataset
uspto-grants-1992_06
Patent number
US05120843

Reaction notes

Loading…