Tetrahydrofuran → HCID 23454741, compound

HRID 1680819Notes

Reaction equation

HRID 1680819 reaction equation
[Li].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:33]=[CH:32][CH:31]=[CH:30][C:12]=3[C:13]=2[N:14]2[CH2:19][CH2:18][N:17]([C:20](=O)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:16][CH2:15]2)=[CH:5][CH:4]=1.O1CCCC1.[OH-].[Na+]>C(OCC)C.O>[ClH:2].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:33]=[CH:32][CH:31]=[CH:30][C:12]=3[C:13]=2[N:14]2[CH2:15][CH2:16][N:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:18][CH2:19]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 3028194LithiumHCID 86737822HCID 86737822, compound

Product 1

HCID 23454741HCID 23454741, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

To the suspension of 9.3 g of lithium aluminumhydride in 200 ml of diethyl ether (anhydr.) is added dropwise the solution of 73.3 g of 1-(2-p-chlorophenyl-3-benzofuryl)-4-pelargonylpiperazine in the mixture of 500 ml of diethyl ether and 200 ml of tetrahydrofuran while stirring at 0°. After addition, the suspension is stirred at ambient temperature for 15 hours, then cooled again to 0° and successively combined with 9.3 ml of water, 9.3 ml of 15% aqueous sodium hydroxide and 27.9 ml of water. The suspension is stirred in the ice-bath for 1 hour, filtered and the residue washed with diethyl ether. The filtrate is dried, evaporated, the residue taken up in the minimum amount of isopropanol and the solution acidified with ethereal hydrogen chloride, to yield the 1-(2-p-chlorophenyl-3-benzofuryl)-4-n-nonylpiperazine hydrochloride melting at 268°-270° with decomposition.

Workup

  1. additionAfter addition
  2. stirringthe suspension is stirred at ambient temperature for 15 hours
  3. temperaturecooled again to 0°
  4. filtrationfiltered
  5. washthe residue washed with diethyl ether
  6. customThe filtrate is dried
  7. customevaporated

Sources & evidence

ORD record
ord-63f8db2cf437427d886a62f835e9a0c0
Source dataset
uspto-grants-1981_06
Patent number
US04276294

Reaction notes

Loading…