Ethanol → 3-[3-(3,4-Dichlorophenyl)-8-azabicyclo[3.2.1]oct-2-en-8-yl]propoxy-1H-indole

HRID 987585Notes

Reaction equation

HRID 987585 reaction equation
ClCCCO[C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2.[Cl:15][C:16]1[CH:17]=[C:18]([C:23]2[CH2:29][CH:28]3[NH:30][CH:25]([CH2:26][CH2:27]3)[CH:24]=2)[CH:19]=[CH:20][C:21]=1[Cl:22].[C:31]([OH:36])(=O)[C:32](O)=O.[CH3:37]CO>>[Cl:15][C:16]1[CH:17]=[C:18]([C:23]2[CH2:24][CH:25]3[N:30]([CH2:37][CH2:32][CH2:31][O:36][N:10]4[C:11]5[C:7](=[CH:6][CH:14]=[CH:13][CH:12]=5)[CH:8]=[CH:9]4)[CH:28]([CH2:27][CH2:26]3)[CH:29]=2)[CH:19]=[CH:20][C:21]=1[Cl:22]

Participants

5

Reactant 4

HCID 702EthanolHCID 971Oxalic AcidHCID 102206573-(3,4-Dichlorophenyl)-2-nortropeneHCID 116941694-(3-chloropropoxy)-1H-indole

Product 1

HCID 865872983-[3-(3,4-Dichlorophenyl)-8-azabicyclo[3.2.1]oct-2-en-8-yl]propoxy-1H-indole

Procedure

The title compound is prepared according to the procedure of Example 2, Step 3, except that 4-(3-chloropropoxy)-1H-indole is used in place of 4-(2-chloro-ethoxy)-1H-indole and 3-(3,4-dichloro-phenyl)-8-aza-bicyclo[3.2.1]oct-2-ene is used in place of 3-(8-aza-bicyclo[3.2.1]oct-2-en-3-yl)-1H-indole. The corresponding oxalate salt is prepared by treating the title compound with 1 equiv. of oxalic acid in EtOH. Yield: 22% of an off-white solid. mp: 150-153° C.; MS (ES) m/z: 427.2 (MH)+.

Workup

  1. customThe title compound is prepared
  2. customThe corresponding oxalate salt is prepared

Sources & evidence

ORD record
ord-de4f7caabf5540f183f3b851a93308ef
Source dataset
uspto-grants-2003_10
Patent number
US06632824B2

Reaction notes

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