Indole → HCID 131719698, compound

HRID 565485Notes

Reaction equation

HRID 565485 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Cl:10][C:11]1[C:21]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16][C:15]=2[CH:14]=[CH:13][C:12]=1[Cl:22].[C:23]([OH:28])(=[O:27])[C:24]([OH:26])=[O:25].[CH3:29]O>C(OCC)(=O)C>[C:23]([OH:28])(=[O:27])[C:24]([OH:26])=[O:25].[NH:1]1[C:9]2[C:4](=[C:5]([O:25][CH2:24][C@@H:23]([OH:28])[CH2:29][N:18]3[CH2:17][CH2:16][C:15]4[CH:14]=[CH:13][C:12]([Cl:22])=[C:11]([Cl:10])[C:21]=4[CH2:20][CH2:19]3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 798IndoleHCID 887MethanolHCID 971Oxalic AcidHCID 9813197180160-89-8

Product 1

HCID 131719698HCID 131719698, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The title compound was prepared in similar fashion from (S)-(+)-4-oxiranylmethoxy)-1H-indole and 6,7-dichloro-2,3,4,5-tetrahydro-1H-3-benzazepine. 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=405 (M+ of free base). α[D]589=−6.87 (c=0.44, methanol).

Sources & evidence

ORD record
ord-e6119018d6f2462395724d814440693b
Source dataset
uspto-grants-2001_01
Patent number
US06172073B2

Reaction notes

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