Triethylamine → 1-Boc-4-[(N-methoxy-N-methylcarbamoyl)methyl]piperidine

HRID 911932Notes

Reaction equation

HRID 911932 reaction equation
Cl.[CH3:2][O:3][NH:4][CH3:5].Cl.C(N=C=NCCCN(C)C)C.O.N1(O)C2C=CC=CC=2N=N1.C(N(CC)CC)C.[C:36]([O:40][C:41]([N:43]1[CH2:48][CH2:47][CH:46]([CH2:49][C:50]([OH:52])=O)[CH2:45][CH2:44]1)=[O:42])([CH3:39])([CH3:38])[CH3:37]>C(Cl)Cl>[CH3:2][O:3][N:4]([CH3:5])[C:50](=[O:52])[CH2:49][CH:46]1[CH2:45][CH2:44][N:43]([C:41]([O:40][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:42])[CH2:48][CH2:47]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 1512539[1-(tert-Butoxycarbonyl)piperidin-4-yl]acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 229287811-Boc-4-[(N-methoxy-N-methylcarbamoyl)methyl]piperidineYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-methoxymethanamine hydrochloride (2.61 g, 26.7 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (5.91 g, 30.8 mmol), 1H-benzo[d][1,2,3]triazol-1-ol hydrate (4.72 g, 30.8 mmol), and triethylamine (11.5 mL, 82.2 mmol) were added sequentially to a solution of 2-(1-(tert-butoxycarbonyl)piperidin-4-yl)acetic acid (5.00 g, 20.6 mmol) in methylene chloride (150 mL) at 0° C. Stirred at ambient temperature for 4 hours, and partitioned between ethyl acetate and 2N HCl. Washed the organic layer again with 2N HCl, twice with 2N NaOH, brine, dried, and concentrated to afford the title compound (5.93 g, 101% yield) as a clear colorless viscous oil.

Workup

  1. custompartitioned between ethyl acetate and 2N HCl
  2. washWashed the organic layer again with 2N HCl
  3. dry with materialtwice with 2N NaOH, brine, dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4f9f897d3f9d404d839b3ac463fb45a4
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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