Triethylamine → tert-butyl N-[[1-[(E)-N'-hydroxycarbamimidoyl]piperidin-4-yl]methyl]carbamate

HRID 1831802Notes

Reaction equation

HRID 1831802 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]#[N:16])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:19][OH:20].C(N(CC)CC)C>C(O)(C)C>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15](=[NH:16])[NH:19][OH:20])[CH2:13][CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 23396324tert-butyl N-[(1-cyanopiperidin-4-yl)methyl]carbamate

Product 1

HCID 178453097tert-butyl N-[[1-[(E)-N'-hydroxycarbamimidoyl]piperidin-4-yl]methyl]carbamate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(1-Cyano-piperidin-4-ylmethyl)-carbamic acid tert-butyl ester (2 g, 8.36 mmol), hydroxylamine hydrochloride (3.48 g, 50.14 mmol) and triethylamine (5.92 g, 58.5 mmol) were stirred in 30 ml of isopropanol at room temperature for 4 hours. The mixture was evaporated. After addition of water (pH4) and ethyl acetate, the organic layer was separated and evaporated.

Workup

  1. customThe mixture was evaporated
  2. additionAfter addition of water (pH4) and ethyl acetate
  3. customthe organic layer was separated
  4. customevaporated

Sources & evidence

ORD record
ord-ecba89ba85b740ff8bc5e1b26c10e478
Source dataset
uspto-grants-2006_06
Patent number
US07067665B2

Reaction notes

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