Aluminum(III) Chloride → 1-{3-[4-(2,3-Dichlorophenyl)piperazin-1-yl]propyl}-2,3-dihydro-1H-indole, Hydrochloride

HRID 1354066Notes

Reaction equation

HRID 1354066 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Cl-].[Cl-].[Al+3].[Cl:11][C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[N:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][C:27]([N:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:31][CH2:30]2)=O)[CH2:21][CH2:20]1>O1CCCC1>[ClH:11].[Cl:11][C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[N:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][N:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:31][CH2:30]2)[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 113271493-[4-(2,3-Dichlorophenyl)piperazin-1-yl]-1-(2,3-dihydro-1H-indol-1-yl)propan-1-one2×HCID 21226445Aluminium lithium hydride

Product 1

HCID 1317258501-{3-[4-(2,3-Dichlorophenyl)piperazin-1-yl]propyl}-2,3-dihydro-1H-indole, Hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

Lithium aluminium hydride (1.8 g) was suspended in tetrahydrofuiran (30 mL) at 0° C., and the suspension was added a solution of aluminium trichloride (1.8 g) in tetrahydrofuran (30 mL) at 0–5° C. over 15 min. To this mixture, a solution of 1a, 3-[4-(2,3-dichlorophenyl)-piperazin-1-yl]-1-(2,3-dihydro-1H-indol-1-yl)propan-1-one (5 g) in tetrahydrofuran (50 mL) was added at a temperature of 0–10° C. The resulting mixture was stirred for 30 min at 5° C. and then for 2 h at room temperature. The reaction mixture was quenched with water and sodium hydroxide (28%) and filtered. The organic phase was evaporated to dryness in vacuo, and the title compound was precipitated as the hydrochloride salt and recrystallised from ethanol (3.8 g). Mp 214–226° C. 1H NMR (DMSO-d6): 2.05–2.20 (m, 2H); 2.95 (t, 2H); 3.10–3.35 (m, 8H); 3.35–3.50 (m, 4H); 3.60 (d, 2H); 6.70 (b s, 2H); 7.05 (t, 1H); 7.10 (d, 1H); 7.20 (d, 1H); 7.30–7.40 (m, 2H); 11.45 (b s). MS m/z: 390 (MH+), 271, 132.

Workup

  1. customwas suspended in tetrahydrofuiran (30 mL) at 0° C.
  2. waitfor 2 h at room temperature
  3. customThe reaction mixture was quenched with water and sodium hydroxide (28%)
  4. filtrationfiltered
  5. customThe organic phase was evaporated to dryness in vacuo
  6. customthe title compound was precipitated as the hydrochloride salt
  7. customrecrystallised from ethanol (3.8 g)

Sources & evidence

ORD record
ord-37d1caab6d2c4e6ebb76de6d02bd789e
Source dataset
uspto-grants-2007_05
Patent number
US07223765B2

Reaction notes

Loading…