4-Amino-1-Boc-piperidine → HCID 178452095, compound

HRID 1896651Notes

Reaction equation

HRID 1896651 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[N:3][CH:2]=1.[NH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1>COC(C)(C)C>[N:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[N:9]/[CH:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]2)=[N:3][CH:2]=1

Participants

4

Reactant 2

HCID 12682914-Amino-1-Boc-piperidineHCID 11412355Pyrimidine-4-carboxaldehyde

Product 1

HCID 178452095HCID 178452095, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Pyrimidine-4-carbaldehyde (C12) (23.00 g, 212.8 mmol) was added to a mixture of tert-butyl 4-aminopiperidine-1-carboxylate (42.61 g, 212.8 mmol) in tert-butyl methyl ether (1.52 L). After 2.5 hours, the reaction was filtered, and the filtrate was concentrated in vacuo to provide an amber oil, which was generally taken directly to the following step. Yield: 56.30 g, 193.9 mmol, 91%. 1H NMR (400 MHz, CDCl3) partial spectrum, characteristic peaks: δ 1.49 (s, 9H), 7.95 (dd, J=5.2, 1.5 Hz, 1H), 8.36 (s, 1H), 8.81 (d, J=5.2 Hz, 1H), 9.28 (d, J=1.5 Hz, 1H).

Workup

  1. filtrationthe reaction was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto provide an amber oil, which

Sources & evidence

ORD record
ord-ea119fc574d64493825f55c21f4db86f
Source dataset
uspto-grants-2013_08
Patent number
US08518944B2

Reaction notes

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