4-Morpholinecarbonyl chloride → HCID 22649548, compound

HRID 393208Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([N:12]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[CH2:13][CH2:14][CH3:15])[CH2:9]2)=[CH:4][CH:3]=1.[N:22]1([C:28](Cl)=[O:29])[CH2:27][CH2:26]O[CH2:24][CH2:23]1>ClCCl.CCN(C(C)C)C(C)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([N:12]([CH2:13][CH2:14][CH3:15])[CH:16]3[CH2:17][CH2:18][N:19]([C:28]([N:22]4[CH2:27][CH2:26][CH2:24][CH2:23]4)=[O:29])[CH2:20][CH2:21]3)[CH2:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of the (7-bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-piperidin-4-yl-propyl-amine (200 μL of 0.25 M in dichloromethane, 50 μmol) was added 220 μL of 0.25 M solution of morpholine 4-carbonyl chloride in dichloromethane and 30 μL of DIEA. The reaction was stirred at 25° C. for 24 h. Concentrated in vacuo. The final product was isolated by preparative RPHPLC (YMC Combiprep ODS-A column, 10-90% acetonitrile: water (0.1% TFA)) to afford {4-[(7-bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-piperidin-1-yl}-pyrrolidin-1-yl-methanone 34 (4.6 mg), [M+H]+=562.

Workup

concentrationConcentrated in vacuo

Sources & evidence

ORD record: ord-4386ef212d414d569c2c5f6d3288801c
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06806278B2

Reaction notes

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