Piperazine → 3-Fluoro-N-[4-(3-piperazin-1-yl-propoxy)-naphthalen-1-yl]-5-piperidin-1-yl-benzamide

HRID 1641262Notes

Reaction equation

HRID 1641262 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([NH:16][C:17](=[O:31])[C:18]2[CH:23]=[C:22]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:21]=[C:20]([F:30])[CH:19]=2)=[CH:8][CH:7]=1.[NH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>>[F:30][C:20]1[CH:19]=[C:18]([CH:23]=[C:22]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:21]=1)[C:17]([NH:16][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[CH:7][CH:8]=1)=[O:31]

Participants

3

Reactant 2

HCID 4837PiperazineHCID 59553319N-[4-(3-chloropropoxy)-naphthalen-1-yl]-3-fluoro-5-piperidin-1-yl-benzamide

Product 1

HCID 595532773-Fluoro-N-[4-(3-piperazin-1-yl-propoxy)-naphthalen-1-yl]-5-piperidin-1-yl-benzamide

Procedure

Compound is prepared from N-[4-(3-chloropropoxy)-naphthalen-1-yl]-3-fluoro-5-piperidin-1-yl-benzamide and piperazine according to conditions described in general procedure L. A yellow powder is produced (0.194 g, 69%). Mp: 70-72° C. 1H NMR (300 MHz, DMSO-d6) δ 10.24 (s, 1H), 8.23 (m, 1H), 7.86 (m, 1H), 7.55 (m, 2H), 7.45 (s, 1H), 7.42 (d, J=8.1 Hz, 1H), 7.16 (d, J=9.0 Hz, 1H), 7.01 (d, J=8.4 Hz, 1H), 6.93 (s, 1H), 4.21 (t, J=6.0 Hz, 2H), 3.32 (m, 4H), 2.71 (t, J=4.5, 4H), 2.53 (m, 2H), 2.35 (brs, 4H), 2.02 (m, J=7.2 Hz, 2H), 1.60 (brs, 6H). MS: 491.2 (M+1).

Workup

  1. customA yellow powder is produced (0.194 g, 69%)

Sources & evidence

ORD record
ord-c35b803857bb4623b9606209f52d828c
Source dataset
uspto-grants-2012_02
Patent number
US08114873B2

Reaction notes

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