Diisopropylethylamine → HCID 67395494, compound

HRID 1403696Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)=[O:19].C(N(C(C)C)CC)(C)C>>[N+:27]([C:24]1[CH:25]=[CH:26][C:21]([O:20][C:18]([NH:1][CH2:2][CH2:3][CH:4]2[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]2)=[O:19])=[CH:22][CH:23]=1)([O-:29])=[O:28]

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 821294-Nitrophenyl chloroformate

HCID 1514258tert-Butyl 4-(2-aminoethyl)piperidine-1-carboxylate

Product 1

HCID 67395494HCID 67395494, compoundYield 99.8%

Procedure

The procedure described in Example 1 (step 1.4.) is followed. Starting from 5 g (21.90 mmol) of tert-butyl 4-(2-aminoethyl)piperidine-1-carboxylate, 4.63 g (23 mmol) of 4-nitrophenyl chloroformate, 5.66 g (43.80 mmol) of diisopropylethylamine and 0.134 g (1.09 mmol) of N,N-dimethylaminopyridine gives 8.6 g of product in the form of an oil which is used as it is in the following step.

Sources & evidence

ORD record: ord-601fd4775b494f7ba704b834819ad0b0
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912218B2

Reaction notes

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