Potassium Iodide → 1-[2-(3,4-Dihydro-1(2H)-benzopyran-4-yl)ethyl]-4-(4-nitrophenyl)-piperazine

HRID 1110792Notes

Reaction equation

HRID 1110792 reaction equation
Br[CH2:2][CH2:3][CH:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][CH2:6][CH2:5]1.[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:19][CH:18]=1)([O-:16])=[O:15].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(=O)CC>[O:7]1[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:4]([CH2:3][CH2:2][N:26]2[CH2:27][CH2:28][N:23]([C:20]3[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:22][CH:21]=3)[CH2:24][CH2:25]2)[CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 804471-(4-Nitrophenyl)piperazineHCID 143302824-(2-bromoethyl)-3,4-dihydro-2H-benzopyran

Product 1

HCID 221542361-[2-(3,4-Dihydro-1(2H)-benzopyran-4-yl)ethyl]-4-(4-nitrophenyl)-piperazineYield 45.7%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The procedure of Example 1 is followed, but starting with 4-(2-bromoethyl)-3,4-dihydro-(2H)-benzopyran (5 g), 1-(4-nitrophenyl)piperazine (4.3 g) and from dry potassium carbonate (1.43 g), followed by potassium iodide (3.43 g) in 2-butanone (200 cc). The residue obtained is chromatographed on a column 4.4 cm in diameter, containing silica gel (100 g), using a dichloromethane-ethyl acetate mixture (50-50 by volume) as eluent, and collecting 20-cc fractions. The fractions between 100 and 300 cc are concentrated to dryness. The residue obtained is crystallized from isopropyl acetate (30 cc). 1-[2-(3,4-Dihydro-1(2H)-benzopyran-4-yl)ethyl]-4-(4-nitrophenyl)-piperazine (3.48 g) is thus obtained in the form of a yellow solid melting at 110° C.

Workup

  1. customThe residue obtained
  2. customis chromatographed on a column 4.4 cm in diameter
  3. additioncontaining silica gel (100 g)
  4. customcollecting 20-cc fractions
  5. concentrationThe fractions between 100 and 300 cc are concentrated to dryness
  6. customThe residue obtained
  7. customis crystallized from isopropyl acetate (30 cc)

Sources & evidence

ORD record
ord-79284085d8fa4e12b030d1715f14412d
Source dataset
uspto-grants-1990_12
Patent number
US04977166

Reaction notes

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