1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 10216398, compound

HRID 988289Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([N:13]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH2:14][CH2:15][CH3:16])[CH2:10]2)=[CH:5][CH:4]=1.[C:23]([N:26]1[CH2:31][CH2:30]C(C(O)=O)[CH2:28][CH2:27]1)(=[O:25])C.CCN=C=NCCCN(C)C.C1C=CC2N([OH:55])N=NC=2C=1>CCN(C(C)C)C(C)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([N:13]([CH2:14][CH2:15][CH3:16])[CH:17]3[CH2:18][CH2:19][N:20]([C:23]([N:26]4[CH2:27][CH2:28][O:55][CH2:30][CH2:31]4)=[O:25])[CH2:21][CH2:22]3)[CH2:10]2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of (7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-piperidin-4-yl-propyl-amine (200 μL of 0.25 M in dimethyl formamide, 50 μmole) was added 1-acetylpiperidine-4-carboxylic acid (220 μL of 0.25M in DMF), 300 μL of EDCI (0.25M in DMF) and 220 uL of HOBT (0.25M in DMF) and 30 μL DIEA. The solution was allowed to stir for 48 h at 25° C. under N2. 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 1-(4-{4-[(7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-piperidine-1-carbonyl}-piperidin-1-yl)-ethanone 2 (5.2 mg ), [M+H]+=456.

Workup

concentrationConcentrated in vacuo

Sources & evidence

ORD record: ord-332abbc027d94324baedba80f0b58fcb
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06635658B2

Reaction notes

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