Triphenylphosphine → 1-[(4-{4-[(1-isopropylpiperidin-4-yl)oxy]phenyl}tetrahydro-2H-pyran-4-yl)methyl]-4-methylpiperazine

HRID 273004Notes

Reaction equation

HRID 273004 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH2:4][CH2:3]1.[CH:22]([N:25]1[CH2:30][CH2:29][CH:28](O)[CH2:27][CH2:26]1)([CH3:24])[CH3:23].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>>[CH:22]([N:25]1[CH2:30][CH2:29][CH:28]([O:21][C:18]2[CH:17]=[CH:16][C:15]([C:9]3([CH2:8][N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]4)[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)=[CH:20][CH:19]=2)[CH2:27][CH2:26]1)([CH3:24])[CH3:23]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 796811-Isopropylpiperidin-4-ol2×HCID 5363146Diisopropyl azodicarboxylateHCID 685768084-{4-[(4-methylpiperazin-1-yl)methyl]tetrahydro-2H-pyran-4-yl}phenol

Product 1

HCID 598374481-[(4-{4-[(1-isopropylpiperidin-4-yl)oxy]phenyl}tetrahydro-2H-pyran-4-yl)methyl]-4-methylpiperazineYield 14%

Procedure

The title compound (72 mg, 14%) was prepared using 4-{4-[(4-methylpiperazin-1-yl)methyl]tetrahydro-2H-pyran-4-yl}phenol, 1-isopropyl-4-hydroxypiperidine (step 1 of intermediate 21), PPh3 and DIAD similarly to the procedure used for intermediate 55. 1H NMR (400 MHz, CDCl3) δ 1.04 (d, 6H), 1.76-1.90 (m, 4H), 1.96-2.08 (m, 4H), 2.17-2.26 (m, 11H), 2.33-2.38 (m, 4H), 2.69-2.80 (m, 3H), 3.51 (t, 2H), 3.69-3.74 (m, 2H), 4.24 (m, 1H), 6.84 (d, 2H), 7.18 (d, 2H). HRMS ESI+ m/z 416.3268 [MH]+.

Sources & evidence

ORD record
ord-c7850029412f482d9a1855e1ce50c4d6
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

Loading…