Formaldehyde → HCID 54704663, compound

HRID 2214705Notes

Reaction equation

HRID 2214705 reaction equation
Cl.Cl.[NH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][NH:6][CH2:5]1.C=O.[CH2:12](N(CC)CC)C.[Cl:19][C:20]1[CH:21]=[C:22]([CH:37]=[CH:38][C:39]=1[Cl:40])[CH2:23][N:24]([CH3:36])[C:25](=[O:35])[CH:26]=[C:27]1[C:31](=[O:32])OC(C)(C)[O:28]1>CO>[Cl:19][C:20]1[CH:21]=[C:22]([CH:37]=[CH:38][C:39]=1[Cl:40])[CH2:23][N:24]([CH3:36])[C:25]([C:26]1[CH2:12][N:3]([CH:4]2[CH2:9][CH2:8][CH2:7][NH:6][CH2:5]2)[C:31](=[O:32])[C:27]=1[OH:28])=[O:35]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 16211870Piperidin-3-amine dihydrochlorideHCID 69655735N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide

Product 1

HCID 54704663HCID 54704663, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred warm (60° C.) solution of 3-aminopiperidine dihydrochloride (150 mg, 0.867 mmol), paraformaldehyde (34 mg, 1.04 mmol) and triethylamine (0.3 mL, 2.14 mmol) in methanol (5 mL) was added N-(3,4-dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide (300 mg, 0.872 mmol). After 1 h, the reaction mixture was cooled and purified by preparative HPLC using a C18 column and water/methanol (0.001 mM HCl) as eluent. The fractions containing the desired product were combined, concentrated and lyophilized to give the corresponding hydrochloride salt of the title compound as a white powder (162 mg, 43% yield). 1HNMR (500 MHz, DMSO-d6) δ: 11.06 (1H, br s), 9.35 (1H, d, J=10.1 Hz), 9.10–8.99 (1H, m), 7.62 (1H, d, J=8.2 Hz), 7.52 (1H, s), 7.29–7.20 (1H, br s), 4.59 (2H, d, JAB=15.7 Hz), 4.34–3.88 (4H, m), 3.40–2.73 (6H, m), 1.90–1.74 (4H, m). HRMS calcd for C18H22Cl2N3O3 (M+H): 398.1038; found: 398.1042.

Workup

  1. temperaturethe reaction mixture was cooled
  2. custompurified by preparative HPLC
  3. additionThe fractions containing the desired product
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c3091a8fedb946fd8bb38428522e6658
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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