Triphenylphosphine → 6-(3-Piperidin-1-yl-propoxy)-quinoline-2-carboxylic acid ethyl ester

HRID 493427Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:16])[CH:12]=2)[N:7]=1)=[O:5])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:36]1([CH2:42][CH2:43][CH2:44]O)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>C1(C)C=CC=CC=1.C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH2:44][CH2:43][CH2:42][N:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)[CH:12]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 35 °C

Procedure

A mixture of 0.400 g (0.002 mol) of 6-hydroxy-quinoline-2-carboxylic acid ethyl ester, 0.966 g (0.004 mmol) of triphenylphospine (Fluka), 0.396 g (0.003 mmol) of 3-piperidin-1-yl-propan-1-ol and 0.68 ml (0.004 mmol) of di-tert.-butyl azadicarboxylate 40% in toluene in 40 ml THF was stirred for a prolonged period of time at 35° C. The mixture was filtered through a pad of silica and washed with 30 ml THF. The mixture was evaporated to dryness and purified on silica eluting with a gradient of DCM/MeOH/NH4OH from 97/3/0.5 to 90/10/0.5. The product fractions were evaporated and the residue was triturated with diethyl ether to yield after drying under vacuum 0.600 g (93%) of the title compound as white solid. MS (m/e): 343.3 (M+H)+.

Workup

filtrationThe mixture was filtered through a pad of silica
washwashed with 30 ml THF
customThe mixture was evaporated to dryness
custompurified on silica eluting with a gradient of DCM/MeOH/NH4OH from 97/3/0.5 to 90/10/0.5
customThe product fractions were evaporated
customthe residue was triturated with diethyl ether
customto yield
dry with materialafter drying under vacuum 0.600 g (93%) of the title compound as white solid

Sources & evidence

ORD record: ord-b00283c4652847368c5c1aa4a71f9cdd
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07534891B2

Reaction notes

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