Hydrochloric Acid → HCID 178491976, compound

HRID 2293522Notes

Reaction equation

HRID 2293522 reaction equation
C(N1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=O.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][N:24]([CH2:27][C:28]([OH:30])=O)[CH2:23][CH2:22]2)=[CH:17][CH:16]=1.[Cl-:31].[NH4+].Cl.C([O:37][CH2:38][CH3:39])(=O)C>C1COCC1.CN(C=O)C>[ClH:31].[ClH:31].[OH:30][C:28](=[C:12]1[CH2:11][C:19]2[C:39](=[CH:17][CH:16]=[CH:15][CH:20]=2)[C:38]1=[O:37])[CH2:27][N:24]1[CH2:23][CH2:22][N:21]([C:18]2[CH:17]=[CH:16][C:15]([O:14][CH3:13])=[CH:20][CH:19]=2)[CH2:26][CH2:25]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8857Ethyl Acetate2×HCID 25517Ammonium ChlorideHCID 682631,1'-CarbonyldiimidazoleHCID 3164603HCID 3164603, compound

Product 1

HCID 178491976HCID 178491976, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
-78 °C

Procedure

Carbonyldiimidazole (1.3 g) was added portionwise to a stirred solution of (4-(4-methoxyphenyl)-piperazin-1-yl)-acetic acid (2.00 g) in 3:1 THF-DMF (40 cm3) at room temperature. After 15 minutes, the solution was cannulated into the above yellow solution. The resulting grey-green slurry was stirred at -78° C. for 15 minutes, then warmed to room temperature and poured into dilute aqueous ammonium chloride (200 cm3). The mixture was extracted with ethyl acetate (100 cm3). The organic extract was dried (MgSO4), filtered and concentrated to give a brown oil. The oil was redissolved in ethyl acetate (50 cm3) and a saturated solution of hydrogen chloride gas in ethyl acetate (50 cm3) was added. After chilling at 0° C. for 24 hours, the brown precipitate was collected to give 2-(1-hydroxy-2-(4-(4-methoxyphenyl)-piperazin-1-yl)-ethylidene)-indan-1-one dihydrochloride (0.82 g; 23%); δH (d6 -DMSO) 3.20-3.70 (8H, m, 2 x NCH2CH2N, partly obscured by H2O signal), 3.62 (2H, s, --CH2 --), 3.71 (3H, s, OCH3), 4.70 (2H, s, --CH2 N), 6.88 (2H, d, J 9, 2 of ArH), 7.03 (2H, d, J 9, 2 of ArH), 7.45 (1H, dd, J 7, 1 of ArH), 7.62-7.59 (2H, m, 2 of ArH) and 8.14 (1H, broad d, J 7, 1 of ArH).

Workup

  1. temperaturewarmed to room temperature
  2. extractionThe mixture was extracted with ethyl acetate (100 cm3)
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a brown oil
  8. temperatureAfter chilling at 0° C. for 24 hours
  9. customthe brown precipitate was collected

Sources & evidence

ORD record
ord-c326a6ad7c8e4307b85df9037817d161
Source dataset
uspto-grants-1997_11
Patent number
US05686480

Reaction notes

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