Formic Acid → HCID 86711148, compound

HRID 625170Notes

Reaction equation

HRID 625170 reaction equation
[C:1]([CH:3]1[NH:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)#[N:2].[OH:16][CH2:17][CH2:18][O:19][CH2:20][CH:21]=O.C(O)=O.C([BH3-])#N.[Na+]>ClCCl.O>[C:1]([CH:3]1[N:8]([CH2:21][CH2:20][O:19][CH2:18][CH2:17][OH:16])[CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)#[N:2]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 176960Acetaldehyde, 2-(2-hydroxyethoxy)-HCID 5003444Sodium cyanoborohydrideHCID 53487922tert-Butyl 3-cyanopiperazine-1-carboxylate

Product 1

HCID 86711148HCID 86711148, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of tert-butyl 3-cyanopiperazine-1-carboxylate, prepared as described in the previous step, (10 g, 0.047 mol) and 2-(2-hydroxyethoxy)acetaldehyde (14.8 g) (see: Bodin, A., Contact Dermatitis, 2001, 44:207) in dichloromethane was treated with formic acid (12.7 g), and the reaction mixture was stirred at room temperature overnight. Sodium cyanoborohydride (7.2 g, 0.118 mol) was added in portions. The reaction mixture was stirred at room temperature for 3 hours followed by the addition of water and extraction with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude product was purified by column chromatography to provide the product.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hours
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography
  7. customto provide the product

Sources & evidence

ORD record
ord-1e69c7802a6642d88f61509299098c04
Source dataset
uspto-grants-2016_04
Patent number
US09304126B2

Reaction notes

Loading…