6-Chloro-m-anisidine → 5-Methoxy-8-{4-[1-(8-quinolinyl)-4-piperidinyl]-1-piperazinyl}-quinoline

HRID 2241999Notes

Reaction equation

HRID 2241999 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2.ClC1C=CC(OC)=CC=1N.[N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][C:37]=2[N:39]2[CH2:44][CH2:43][C:42](=O)[CH2:41][CH2:40]2)[CH:32]=[CH:31][CH:30]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:14][CH2:15][N:16]([CH:42]3[CH2:41][CH2:40][N:39]([C:37]4[CH:36]=[CH:35][CH:34]=[C:33]5[C:38]=4[N:29]=[CH:30][CH:31]=[CH:32]5)[CH2:44][CH2:43]3)[CH2:17][CH2:18]2)=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2

Participants

5

Reactant 4

HCID 754606-Chloro-m-anisidineHCID 5049666Sodium triacetoxyborohydrideHCID 592048421-Quinolin-8-yl-piperidin-4-oneHCID 592048625-Methoxy-8-(piperazin-1-yl)quinoline

Product 1

HCID 120041715-Methoxy-8-{4-[1-(8-quinolinyl)-4-piperidinyl]-1-piperazinyl}-quinoline

Procedure

Using the synthetic methods described in previous examples, 5-methoxy-8-(piperazin-1-yl)quinoline (prepared from 2-chloro-5-methoxyaniline using the methodology described for the preparation of Example N, Step 3, above) and 1-quinolin-8-yl-piperidin-4-one (Example A, Step 5, above) were reacted with sodium triacetoxyborohydride to give the desired product as a beige solid; MP. 218-220° C.; MS (ES) m/z (relative intensity) 454 (M+H)+ (100).

Workup

  1. customdescribed for the preparation of Example N, Step 3

Sources & evidence

ORD record
ord-710b00df19bf4baabe5563341ad50e24
Source dataset
uspto-grants-2010_03
Patent number
US07671056B2

Reaction notes

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