HCID 21922941, compound → HCID 178478690, compound

HRID 1244946Notes

Reaction equation

[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH2:8])[CH2:4][CH2:3]1.[Cl:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][N:16]2[CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[C:12]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][C:32]#[N:33])=[CH:27][CH:26]=2)[N:11]=1>O>[ClH:9].[ClH:9].[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:10]2[N:18]=[C:17]3[C:13]([N:14]=[CH:15][N:16]3[CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)=[C:12]([NH:24][C:25]3[CH:26]=[CH:27][C:28]([CH2:31][C:32]#[N:33])=[CH:29][CH:30]=3)[N:11]=2)[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 140 °C

Procedure

684 mg of trans-1,4-diaminocyclohexane is taken to approximately 140° C. then 211 mg of the product obtained in Stage 1 above is added, the reaction medium is maintained under agitation at 140° C. for 6 hours then left to return to ambient temperature. Then 10 ml of water is added, followed by extracting with dichloromethane, drying and evaporating the solvent. The residue is chromatographed on silica (eluent: MeOH/NH4OH 98/2), followed by taking up in 6 ml of an ethanolic solution of hydrochloric acid, evaporating the solvents, impasting the residue in ether, drying under reduced pressure at 60° C. and 199 mg of expected product is recovered.

Workup

customis taken to approximately 140° C.
waitthen left
customto return to ambient temperature
extractionby extracting with dichloromethane
customdrying
customevaporating the solvent
customThe residue is chromatographed on silica (eluent: MeOH/NH4OH 98/2)
customevaporating the solvents
customdrying under reduced pressure at 60° C.
custom199 mg of expected product is recovered

Sources & evidence

ORD record: ord-7159d418d9034f4db57b5a0b9fdb3826
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122669B1

Reaction notes

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