Sodium Iodide → 8-[3-[4-(3-Methylphenyl)-1-piperazinyl]propyloxy]-8-azaspiro[4.5]decan-7,9-dione hydrochloride hemihydrate

HRID 1761437

Reaction equation

HRID 1761437 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][N:6]1[C:15](=[O:16])[CH2:14][C:9]2([CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:8][C:7]1=[O:17].[ClH:18].Cl.[CH3:20][C:21]1[CH:22]=[C:23]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH:24]=[CH:25][CH:26]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CCN(CC)CC.CC#N>[OH2:5].[ClH:18].[CH3:20][C:21]1[CH:22]=[C:23]([N:27]2[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH2:4][O:5][N:6]3[C:15](=[O:16])[CH2:14][C:9]4([CH2:13][CH2:12][CH2:11][CH2:10]4)[CH2:8][C:7]3=[O:17])[CH2:29][CH2:28]2)[CH:24]=[CH:25][CH:26]=1.[CH3:20][C:21]1[CH:22]=[C:23]([N:27]2[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH2:4][O:5][N:6]3[C:15](=[O:16])[CH2:14][C:9]4([CH2:13][CH2:12][CH2:11][CH2:10]4)[CH2:8][C:7]3=[O:17])[CH2:29][CH2:28]2)[CH:24]=[CH:25][CH:26]=1.[ClH:18]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 831101-(m-Tolyl)piperazine dihydrochlorideHCID 142805838-(3-Bromopropyloxy)-8-azaspiro[4.5]decan-7,9-dione

Product 1

HCID 1317159328-[3-[4-(3-Methylphenyl)-1-piperazinyl]propyloxy]-8-azaspiro[4.5]decan-7,9-dione hydrochloride hemihydrate

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 8-(3-bromopropyloxy)-8-azaspiro[4.5]decan-7,9-dione (5.0 g), 1-(3-methylphenyl)piperazine dihydrochloride (4.11 g), K2CO3 (9.1 g), NaI (100 mg) and n-Bu4NBr (100 mg) in 100 ml of dry tolune was heated at 80° with stirring under N2. After 4 hours, 50 ml of CH3CN was added. Heating was continued for 18 hr. and 5 ml of Et3N was added. Heating was continued for an additional 6 hr and at which time no starting material remained by TLC. The mixture was cooled to room temperature and filtered. The solvents were removed in vacuo and the residue was chromatographed on silica using ethyl acetate as the eluent. The fractions containing the desired product were combined and concentrated in vacuo.

Workup

  1. temperaturewas heated at 80°
  2. temperatureHeating
  3. waitwas continued for 18 hr
  4. temperatureHeating
  5. waitwas continued for an additional 6 hr and at which time
  6. filtrationfiltered
  7. customThe solvents were removed in vacuo
  8. customthe residue was chromatographed on silica
  9. additionThe fractions containing the desired product
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1130f591a1a14fe580015499fe06b735
Source dataset
uspto-grants-1989_05
Patent number
US04826846

Linked notes

Loading…