Ammonium Chloride → HCID 58418632, compound

HRID 2176061Notes

Reaction equation

HRID 2176061 reaction equation
[Li][CH2:2]CCC.[CH3:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=2)[CH2:9][CH2:8]1.[NH4+].[Cl-]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH3:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[CH2:2])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 7365334-(4-Methylpiperazin-1-yl)benzaldehydeHCID 178418339Butyllithium

Product 1

HCID 58418632HCID 58418632, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Dropwise, 39 ml of n-BuLi (1.7 M, 66 mmol) was added to a stirred, cold (0° C.) solution of methyltriphenylphosphonium bromide (23.2 g, 65 mmol) in 100 ml of THF (dried) under N2. After 15 min, a solution of 4-(4-methylpiperazinyl)benzaldehyde (11.9 g, 58 mmol) in 30 ml of THF was added dropwise via needle. The yellow suspension was stirred for 4 hours and treated with NH4Cl. The solution was filtered and concentrated under vacuum. The residue was purified by silica gel column chromatography elution with hexane, EtOAc, and Et3N in a 70:20:10 ratio to yield 10.6 g (90%) of white solid product. Without being bound by theory, it is believed that the following reaction took place.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by silica gel column chromatography elution with hexane, EtOAc, and Et3N in a 70:20:10 ratio

Sources & evidence

ORD record
ord-3c7bf02fa7b345c0938f20320e9a7be6
Source dataset
uspto-grants-2015_06
Patent number
US09062144B2

Reaction notes

Loading…