Formaldehyde → HCID 54704619, compound

HRID 2214704Notes

Reaction equation

HRID 2214704 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH2:13]=O.[Cl:15][C:16]1[CH:17]=[C:18]([CH:33]=[CH:34][C:35]=1[Cl:36])[CH2:19][N:20]([CH3:32])[C:21](=[O:31])[CH:22]=[C:23]1[C:27](=[O:28])OC(C)(C)[O:24]1>CO>[CH2:11]([O:10][C:8]([N:5]1[CH2:4][CH2:3][CH:2]([N:1]2[CH2:13][C:22]([C:21](=[O:31])[N:20]([CH2:19][C:18]3[CH:33]=[CH:34][C:35]([Cl:36])=[C:16]([Cl:15])[CH:17]=3)[CH3:32])=[C:23]([OH:24])[C:27]2=[O:28])[CH2:7][CH2:6]1)=[O:9])[CH3:12]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 69655735N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide

Product 1

HCID 54704619HCID 54704619, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred warm (60° C.) solution of ethyl 4-amino-1-piperidinecarboxylate (86.1 mg, 0.5 mmol) and paraformaldehyde (16 mg, 0.5 mmol) in methanol (2 mL) was added N-(3,4-dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide (175 mg, 0.5 mmol). After 2 h, the reaction mixture was cooled and purified using preparative HPLC on a C18 column using water/methanol-(0.1% TFA) as the eluent. The fractions containing the desired product were combined, concentrated and lyophilized to give the title compound as a white powder (64 mg, 27% yield). 1HNMR (500 MHz, CDCl3) δ: 10.16 (2H, br s), 7.40 (1H, d, J=8.2 Hz), 7.35 (1H, s), 7.10 (1H, d, J=8.0 Hz), 4.59 (2H, s), 4.34–4.18 (3H, m), 4.13 (2H, q, J=7.0 Hz), 4.09 (2H, s), 2.06 (2H, s), 2.87–2.80 (2H, br m), 1.82–1.76 (2H, br m), 1.63–1.55 (2H, m), 1.25 (3H, t, J=7.0 Hz). MS calcd for C21H26Cl2N3O5 (M+H): 470.36. found: 470.02.

Workup

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

Sources & evidence

ORD record
ord-32174c02edb84431941850d3bae13f3c
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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