Triethylamine → HCID 178491966, compound

HRID 2293523Notes

Reaction equation

HRID 2293523 reaction equation
Cl.Cl.O[C:4](=[C:20]1[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]1=O)[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.O.[NH2:31][NH2:32].C(N(CC)CC)C.CO.CN(C=O)C>O>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([N:9]2[CH2:8][CH2:7][N:6]([CH2:5][C:4]3[C:20]4[CH2:28][C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[C:21]=4[NH:31][N:32]=3)[CH2:11][CH2:10]2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 21901440N,N-dimethylformamide methanolHCID 178491976HCID 178491976, compound

Product 1

HCID 178491966HCID 178491966, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 2-(1-hydroxy-2-(4-(4-methoxyphenyl)-piperazin-1-yl)-ethylidene)-indan-1-one dihydrochloride (0.30 g), hydrazine monohydrate (1 cm3) and triethylamine (0.30 cm3) in 1:1 methanol-DMF (10 cm3) was stirred at room temperature under argon for 24 hours. The solution was poured into water (25 cm3) and extracted with ethyl acetate (2×25 cm3). The extracts were dried (MgSO4), filtered and concentrated. Flash column chromatography on silica gel, eluting with 2% methanol-dichloromethane, gave a yellow solid, which was recrystallised from ethanol-water to give the title compound (0.07 g; 29%) as yellow crystals, m.p. 176°-178° C. (from EtOH-H2O); δH (360 MHz, d6 -DMSO) 2.55-2.58 (4H, m, 2 x NCH2 CH2N), 3.01-3.04 (4H, m, 2 x NCH2CH2N), 3.27 (2H, s, --CH2 --, partly obscured by H2O signal), 3.58 (2H, s, --CH2N), 3.67 (3H, s, OCH3), 6.79 (2H, d, JAB 9.2, 2 of ArH), 6.87 (2H, d, JAB 9.2, 2 of ArH), 7.24 (1H, dd, J 7.4 and 7.4, 1 of ArH), 7.32 (1H, dd, J 7.4 and 7.4, 1 of ArH), 7.51 (1H, d, J 7.4, 1 of ArH), 7.59 (1H, broad d, J 7.4, 1 of ArH) and 12.58 (1H, broad s, NH); m/z (CI+ ; NH3) 361 (MH+ ; 23%), 214 (30) and 193 (100).

Workup

  1. extractionextracted with ethyl acetate (2×25 cm3)
  2. dry with materialThe extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washFlash column chromatography on silica gel, eluting with 2% methanol-dichloromethane
  6. customgave a yellow solid, which
  7. customwas recrystallised from ethanol-water

Sources & evidence

ORD record
ord-4563b36152d14646a61b78d51e71a360
Source dataset
uspto-grants-1997_11
Patent number
US05686480

Reaction notes

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