Indole → (2s)-(-)-1-(4-Indolyloxy)-3-(4-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]piperazin-1-yl)-2-propanol ethanedioate

HRID 1779565Notes

Reaction equation

HRID 1779565 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[O:10]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][CH2:12][CH:11]1[CH2:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.[C:27]([OH:32])(=[O:31])[C:28]([OH:30])=[O:29].[CH3:33]O>C(OCC)(=O)C>[C:27]([OH:32])(=[O:31])[C:28]([OH:30])=[O:29].[NH:1]1[C:9]2[C:4](=[C:5]([O:29][CH2:28][C@@H:27]([OH:32])[CH2:33][N:24]3[CH2:23][CH2:22][N:21]([CH2:20][CH:11]4[O:10][C:15]5[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=5[O:13][CH2:12]4)[CH2:26][CH2:25]3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 798IndoleHCID 887MethanolHCID 971Oxalic AcidHCID 4106821-(1,4-Benzodioxan-2-ylmethyl)piperazine

Product 1

HCID 131719665(2s)-(-)-1-(4-Indolyloxy)-3-(4-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]piperazin-1-yl)-2-propanol ethanedioate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The title compound was prepared in similar fashion from S)-(+)-4-(oxiranylmethoxy)-1H)indole and 1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]piperazine. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 77% overall yield. FDMS m/e=423 (M+ of free base). α[D]589 =-10.21 (c=0.82, methanol).

Sources & evidence

ORD record
ord-12ef9a3d352e4fed952c0336e0c27fc8
Source dataset
uspto-grants-1997_05
Patent number
US05627196

Reaction notes

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