4-(Dimethylamino)Benzaldehyde → n-(5-Carboxypentyl)-4-(4-(dimethylamino)styryl)pyridinium bromide

HRID 1818646Notes

Reaction equation

[CH3:1][N:2]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=O)=[CH:6][CH:5]=1)[CH3:3].[Br-:12].[C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N+:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1C)([OH:15])=[O:14].N1CCCC[CH2:29]1>C(O)C>[Br-:12].[C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N+:21]1[CH:22]=[CH:23][C:24]([CH:29]=[CH:10][C:7]2[CH:6]=[CH:5][C:4]([N:2]([CH3:1])[CH3:3])=[CH:9][CH:8]=2)=[CH:25][CH:26]=1)([OH:15])=[O:14]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-N,N-dimethylaminobenzaldehyde (3 g, 20 mmoles), N-(5-carboxypentyl)picolinium bromide (5.6 g, 20 mmoles) and piperidine (2 mL) in ethanol (100 mL) was heated at 60° C. overnight. The mixture was evaporated to dryness in vacuo. The residue was redissolved in methanol and then precipitated with ether to give the title product (6.7 g).

Workup

customThe mixture was evaporated to dryness in vacuo
dissolutionThe residue was redissolved in methanol
customprecipitated with ether

Sources & evidence

ORD record: ord-8cde525a242549cbaf98a743a5544eef
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601498B2

Reaction notes

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