Morpholine → 3-(8-Chloro-1, 2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)-1-morpholinopropan-1-one

HRID 710792Notes

Reaction equation

HRID 710792 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH2:12][C:13]([OH:15])=O)[C:6]3[CH2:16][CH2:17][N:18]([CH3:20])[CH2:19][C:5]=3[C:4]=2[CH:3]=1.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH2:12][C:13]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[O:15])[C:6]3[CH2:16][CH2:17][N:18]([CH3:20])[CH2:19][C:5]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 10868DicyclohexylcarbodiimideHCID 59161642HCID 59161642, compound

Product 1

HCID 578759243-(8-Chloro-1, 2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)-1-morpholinopropan-1-oneYield 8.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)propanoic acid (100 mg, 0.34 mmol), morpholine (29 mg, 0.34 mmol), DCC (77 mg, 0.37 mmol), and DMAP (46 mg, 0.37 mmol) in dry DCM (2.5 mL) was stirred at room temperature for 3 h. The reaction mixture was filtered through Celite and concentrated by rota vapor to obtain 10 mg of 3-(8-chloro-1, 2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)-1-morpholinopropan-1-one as TFA salt after purification by reverse-phase chromatography (C-18, 500 mm×50 mm, Mobile Phase A=0.05% TFA in water, B=0.05% TFA in acetonitrile, Gradient: 10% B to 80% B in 30 min, injection vol. 5 mL).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated by rota vapor

Sources & evidence

ORD record
ord-7925311e5f3a42389713d7a55d1b9d95
Source dataset
uspto-grants-2015_11
Patent number
US09181240B2

Reaction notes

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