1-Bromo-3-chloropropane → 9-(3-Chloro-propoxy)-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indol-1-one

HRID 2105355Notes

Reaction equation

[OH:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:16])[C:6]3=[CH:5][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH2:25][CH2:26][Cl:27]>>[Cl:27][CH2:26][CH2:25][CH2:24][O:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:16])[C:6]3=[CH:5][C:4]=2[CH:3]=1

Participants

Reactant 3

HCID 80061-Bromo-3-chloropropane

HCID 11430Potassium Carbonate

HCID 684670999-Hydroxy-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indol-1-one

Product 1

HCID 684636919-(3-Chloro-propoxy)-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indol-1-oneYield 35%

Procedure

The title compound was synthesized in analogy to example 2, intermediate, from 9-hydroxy-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indol-1-one (example 15, intermediate a)), potassium carbonate and 1-bromo-3-chloropropane, to give the desired compound as a light yellow solid (35%).

Sources & evidence

ORD record: ord-3e14f687169848c1b67df0b67d71f818
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579351B2

Reaction notes

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