Ethylamine → tert-Butyl 4-(ethylamino)piperidine-1-carboxylate

HRID 2185543Notes

Reaction equation

HRID 2185543 reaction equation
[CH2:1]([NH2:3])[CH3:2].CCN(C(C)C)C(C)C.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[CH2:1]([NH:3][CH:23]1[CH2:24][CH2:25][N:20]([C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[CH2:21][CH2:22]1)[CH3:2]

Participants

7

Reactant 4

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18374730tert-Butyl 4-(ethylamino)piperidine-1-carboxylateYield 111.1%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Ethylamine (10 mL, 1 M in THF, 10 mmol) and DIEA (2.3 mL, 13.4 mmol) were dissolved in 100 mL of 1,2-dichloroethane under nitrogen. A solution of 1-tert-butoxycarbonyl-4-piperidone (1.3 g, 6.7 mmol) in 100 mL of 1,2-dichloroethane was added, followed by sodium triacetoxyborohydride (4.2 g, 20 mmol). The mixture was stirred at rt under nitrogen for 14 h, then diluted with CH2Cl2. The solution was washed twice with each of 1 N NaOH and brine, dried over Na2So4 and concentrated to afford 1.7 g (97%) of the title compound.

Workup

  1. washThe solution was washed twice with each of 1 N NaOH and brine
  2. customdried over Na2So4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9a6e5b26e0fd400f97a5798906b22848
Source dataset
uspto-grants-2002_06
Patent number
US06399619B1

Reaction notes

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