Triethylamine → 4-[(glycylamino)methyl]-1-[4-(N-phenylcarbamoyl)benzyl]piperidine

HRID 1281004Notes

Reaction equation

C1C2C(COC([NH:18][CH2:19][C:20]([NH:22][CH2:23][CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[O:21])=O)C3C(=CC=CC=3)C=2C=CC=1.CCN(CC)CC.[C:37]1([NH:43][C:44]([C:46]2[CH:53]=[CH:52][C:49]([CH2:50]Cl)=[CH:48][CH:47]=2)=[O:45])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CC#N>[NH2:18][CH2:19][C:20]([NH:22][CH2:23][CH:24]1[CH2:25][CH2:26][N:27]([CH2:50][C:49]2[CH:48]=[CH:47][C:46]([C:44](=[O:45])[NH:43][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)=[CH:53][CH:52]=2)[CH2:28][CH2:29]1)=[O:21]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 4-[{N-(9-fluorenylmethyloxycarbonyl)glycyl}aminomethyl]piperidine (1.27 g, 2.96 mmol), Et3N (1.25 mL, 8.88 mmol), KI (50 mg, 0.30 mmol) and CH3CN (200 mL) was added dropwise a solution of 4-(N-phenylcarbamoyl)benzyl chloride (800 mg, 3.26 mmol) in CH3CN (100 mL). The mixture was stirred at room temperature for 19 h and at 60° C. for 5 h. Concentration and column chromatography (SiO2, 5% CH3OH/CH2Cl2-Et3N:CH3OH:CH2C2=2:2:96) afforded 4-{(glycylamino)methyl}-1-{4-(N-phenylcarbamoyl)benzyl}piperidine (340 mg, 30%).

Workup

concentrationConcentration and column chromatography (SiO2, 5% CH3OH/CH2Cl2-Et3N:CH3OH:CH2C2=2:2:96)

Sources & evidence

ORD record: ord-f044e893e30c478daec5f66c6ea11a14
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06451842B1

Reaction notes

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