Methyl Isocyanate → HCID 21362789, compound

HRID 983466Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([N:13]([CH2:17][CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH2:14][CH2:15][CH3:16])[CH2:10]2)=[CH:5][CH:4]=1.[CH3:24][N:25]=[C:26]=[O:27]>ClCCl.C(#N)C.CCN(C(C)C)C(C)C>[CH3:24][NH:25][C:26]([N:21]1[CH2:20][CH2:19][CH:18]([CH2:17][N:13]([CH:9]2[CH2:8][CH2:7][C:6]3[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:10]2)[CH2:14][CH2:15][CH3:16])[CH2:23][CH2:22]1)=[O:27]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of (7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-piperidin-4-ylmethyl-propyl-amine (200 μL of a 0.25 M solution in dichloromethane, 50 μmole) was added 220 μL of a 0.25 M solution of methyl isocyanate in acetonitrile and 30 μL of DIEA. The solution was allowed to stir for 24 h at 25° C. under N2 and then 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-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-methyl}-piperidine-1-carboxylic acid methylamide (17.1 mg) 25 [M+H]+=374.

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d37a1e28ecbd493e9f4c83c533d54c2c
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06864266B2

Reaction notes

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