1-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine → (7-Chloro-4-methoxymethyl-quinolin-2-yl)-[1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-yl]-amine

HRID 913074Notes

Reaction equation

HRID 913074 reaction equation
Cl[C:2]1[CH:11]=[C:10]([CH2:12][O:13][CH3:14])[C:9]2[C:4](=[CH:5][C:6]([Cl:15])=[CH:7][CH:8]=2)[N:3]=1.[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]1)[CH3:17]>CN1C(=O)CCC1>[Cl:15][C:6]1[CH:5]=[C:4]2[C:9]([C:10]([CH2:12][O:13][CH3:14])=[CH:11][C:2]([NH:29][CH:26]3[CH2:27][CH2:28][N:23]([CH2:22][C:21]4[CH:30]=[CH:31][C:32]([O:33][CH3:34])=[C:19]([O:18][CH2:16][CH3:17])[CH:20]=4)[CH2:24][CH2:25]3)=[N:3]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 392574451-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine2×HCID 866185572,7-Dichloro-4-methoxymethyl-quinoline

Product 1

HCID 24855023(7-Chloro-4-methoxymethyl-quinolin-2-yl)-[1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-yl]-amineYield 14%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 2,7-dichloro-4-methoxymethyl-quinoline (36.3 mg, 0.15 mmol, 1.0 equiv) and 1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine (47.6 mg, 0.18 mmol, 1.5 equiv; intermediate A1) in NMP (2 mL) was heated by microwave irradiation to 200° C. for 30 min. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 9.6 mg (14%) of the title compound. MS (ISP): 470.4 [M+H]+.

Workup

  1. customRemoval of the solvent
  2. customunder reduced pressure and purification by preparative HPLC on reversed phase
  3. washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-d1f6bf53ec634076843eaa5c4c481815
Source dataset
uspto-grants-2011_09
Patent number
US08026255B2

Reaction notes

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