p-Bromochlorobenzene → HCID 9964563, compound

HRID 1883448Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1.[NH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:9][CH2:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:3][CH:4]=1

Participants

Reactant 2

HCID 7806p-Bromochlorobenzene

HCID 235274-(Aminomethyl)piperidine

Product 1

HCID 9964563HCID 9964563, compoundYield 62%

Procedure

Using the general procedure, 4-bromochlorobenzene (192 mg, 1.0 mmol) was coupled with 4-aminomethylpiperidine (171 mg, 1.5 mmol). Purification of the crude product by column chromatography on silica gel using methanol/dichloromethane (saturated with ammonia) (1:20) as eluent afforded the desired product as a light yellow solid (138 mg, 62% yield). Rf=0.3 (methanol/dichloromethane (saturated with ammonia) (1:20)).

Workup

customPurification of the crude product by column chromatography on silica gel

Sources & evidence

ORD record: ord-f2118482e7ad40b6ae9a196e745a73ce
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06759554B2

Reaction notes

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