Diisopropylethylamine → HCID 11952786, compound

HRID 1354063Notes

Reaction equation

HRID 1354063 reaction equation
Cl.[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(N(C(C)C)CC)(C)C.Br[CH2:26][CH2:27][CH2:28][CH2:29][C:30]([N:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][CH2:33]1)=[O:31]>CC(=O)CC>[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:26][CH2:27][CH2:28][CH2:29][C:30]([N:32]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:34][CH2:33]2)=[O:31])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 116303721-(2,3-Dichlorophenyl)piperazine hydrochlorideHCID 22029304HCID 22029304, compound

Product 1

HCID 11952786HCID 11952786, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 1-(2,3-dichlorophenyl)piperazine hydrochloride (8.0 g) and diisopropylethylamine (15 mL) in butanone (50 mL) was heated to 45° C. followed by the addition of 5-bromo-1-(2,3-dihydro-1H-indol-1-yl)pentan-1-one (5.4 g). The resulting mixture was boiled under reflux for 40 h and filtered hot. The remaining organic phase was left to crystallise, and a white crystalline material was collected by filtration and washed with acetone (3.8 g). Mp 121–123° C. 1H NMR (DMSO-d6): 1.50–1.70 (m, 4H); 2.30–2.65 (m, 8H); 3.00 (s, 4H); 3.15 (t, 2H); 4.10 (t, 2H); 6.95 (t, 1H); 7.10–7–15 (m, 2H); 7.20 (d, 1H); 7.25–7.35 (m, 2H); 8.10 (d, 1H). MS m/z: 432 (MH+), 315, 202.

Workup

  1. temperatureunder reflux for 40 h
  2. filtrationfiltered hot
  3. waitThe remaining organic phase was left
  4. customto crystallise
  5. filtrationa white crystalline material was collected by filtration
  6. washwashed with acetone (3.8 g)

Sources & evidence

ORD record
ord-2c79c8171908420d94e8a62ad64f3174
Source dataset
uspto-grants-2007_05
Patent number
US07223765B2

Reaction notes

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