Diisopropylethylamine → 1-tert-Butoxycarbonyl-4-[N-methyl-N-(3-(formyl)-2-pyridinyl)amino]piperidine

HRID 361801Notes

Reaction equation

Br[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([NH:23][CH3:24])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(N(C(C)C)CC)(C)C>>[C:10]([O:14][C:15]([N:17]1[CH2:18][CH2:19][CH:20]([N:23]([CH3:24])[C:2]2[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:21][CH2:22]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 47149512-Bromonicotinaldehyde

HCID 15380702tert-Butyl 4-(methylamino)piperidine-1-carboxylate

Product 1

HCID 104958741-tert-Butoxycarbonyl-4-[N-methyl-N-(3-(formyl)-2-pyridinyl)amino]piperidine

Procedure

Following the general procedure of EXAMPLE 12 and making non-critical variations but starting with 2-bromo-3-formylpyridine (XVI, EXAMPLE 1, 2.67 g, 14.4 mmol), 1-tert-butoxycarbonyl-4-methylaminopiperidine (XIII, 2.8 g, 13.1 mmol), and diisopropylethylamine (2.3 ml), the title compound is obtained, mp 90°-91°.

Sources & evidence

ORD record: ord-fc54829d51c7473db70750a1eeb56143
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05866589

Reaction notes

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