1-(2-Bromoethyl)-3-chlorobenzene → 8-(3-[1-[2-(3-Chlorophenyl)ethyl]-4-piperidinyl]propanoyl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one hydrochloride

HRID 719819Notes

Reaction equation

HRID 719819 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][C:9]([C:11]2[CH:12]=[C:13]3[C:18]4=[C:19]([CH2:21][CH2:22][N:17]4[C:16](=[O:23])[CH2:15][CH2:14]3)[CH:20]=2)=[O:10])[CH2:3][CH2:2]1.Br[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=1>>[ClH:33].[Cl:33][C:29]1[CH:28]=[C:27]([CH2:26][CH2:25][N:1]2[CH2:2][CH2:3][CH:4]([CH2:7][CH2:8][C:9]([C:11]3[CH:12]=[C:13]4[C:18]5=[C:19]([CH2:21][CH2:22][N:17]5[C:16](=[O:23])[CH2:15][CH2:14]4)[CH:20]=3)=[O:10])[CH2:5][CH2:6]2)[CH:32]=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 1401401-(2-Bromoethyl)-3-chlorobenzeneHCID 99665448-[3-(4-piperidinyl)propanoyl]1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one

Product 1

HCID 218877348-(3-[1-[2-(3-Chlorophenyl)ethyl]-4-piperidinyl]propanoyl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one hydrochlorideYield 84.3%

Procedure

Using 8-[3-(4-piperidinyl)propanoyl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one (500 mg) and 1-(2-bromoethyl)-3-chlorobenzene (394 mg) according to the same method as that of Example 81, the title compound (369 mg) was obtained as colorless crystals having a melting point of 223 to 225° C.

Sources & evidence

ORD record
ord-942a00bb2eaf4246b31c326735c8b549
Source dataset
uspto-grants-2006_11
Patent number
US07132547B2

Reaction notes

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