Hydrochloric Acid → HCID 86751327, compound

HRID 1418585Notes

Reaction equation

[ClH:1].[F:2][C:3]([F:44])([F:43])[C:4]1[CH:5]=[C:6]([CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=1)[C:7]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]=CC2C=CC=CC=2O)[CH2:11][C@H:10]1[CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1)=[O:8].C(OCC)(=O)C.CO>O1CCOCC1>[ClH:1].[ClH:1].[NH2:17][CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][N:9]([C:7](=[O:8])[C:6]2[CH:5]=[C:4]([C:3]([F:43])([F:44])[F:2])[CH:38]=[C:37]([C:39]([F:40])([F:41])[F:42])[CH:36]=2)[C@H:10]([CH2:26][C:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[NH:29][CH:28]=2)[CH2:11]1

Participants

Conditions

Temperature: 50 °C

Procedure

Hydrochloric acid (0.22 ml) was added to a stirred mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-[N-(2-hydroxybenzylidene)-2-aminoethyl]-2-(1H-indol-3-yl-methyl)piperazine (0.80 g), ethyl acetate (12 ml) and methanol (6 ml) at room temperature. The mixture was stirred at 50° C. for 4.5 hours and then concentrated in vacuo to give an oil. The oil was treated with 4N hydrogen chloride in dioxane solution (0.33 ml) to afford (2R)-4-(2-aminoethyl)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)piperazine dihydrochloride (0.57 g).

Workup

concentrationconcentrated in vacuo
customto give an oil

Sources & evidence

ORD record: ord-8639c8106a664f608de1dea7f52e3dba
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05883098

Reaction notes

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