Methanol → HCID 131719674, compound

HRID 1900929Notes

Reaction equation

HRID 1900929 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][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]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:19]=[CH:20][C:21]=1[Cl:22].[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31].CO>C(OCC)(=O)C>[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31].[NH:10]1[C:11]2[C:7](=[C:6]([O:5][CH2:4][C@@H:2]([OH:1])[CH2:3][N:26]3[CH2:25][CH2:24][N:23]([C:18]4[CH:19]=[CH:20][C:21]([Cl:22])=[C:16]([Cl:15])[CH:17]=4)[CH2:28][CH2:27]3)[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

Participants

6

Reactant 4

HCID 887MethanolHCID 971Oxalic AcidHCID 936011-(3,4-Dichlorophenyl)piperazineHCID 10943254(2s)-Glycidyl indol-4-yl ether

Product 1

HCID 131719674HCID 131719674, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and 1-(3,4-dichlorophenyl)piperazine. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 87% overall yield. FDMS m/e=419 (M+ of free base). α[D]589 =-7.76 (c=0.82, methanol).

Sources & evidence

ORD record
ord-76b1561a64b34074a9391dcfec0675db
Source dataset
uspto-grants-1996_11
Patent number
US05576321

Reaction notes

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