Formaldehyde → HCID 59341466, compound

HRID 15249Notes

Reaction equation

HRID 15249 reaction equation
[CH3:1][N:2]([CH3:21])[C:3]([CH2:19][CH3:20])([CH2:16][CH:17]=[CH2:18])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][CH2:14][OH:15])=[CH:8][CH:7]=1)=[O:5].C=O.[C:24]([BH3-])#N.[Na+]>C1COCC1.C(#N)C.O.C(Cl)Cl>[CH3:1][N:2]([CH3:21])[C:3]([CH2:19][CH3:20])([CH2:16][CH:17]=[CH2:18])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]([CH2:13][CH2:14][OH:15])[CH3:24])=[CH:8][CH:7]=1)=[O:5]

Participants

8

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 59341488HCID 59341488, compound

Product 1

HCID 59341466HCID 59341466, compoundYield 75.6%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

In a 300 ml sulfonation under argon atmosphere, 2.90 g (10 mmol) of 2-dimethylamino-2-ethyl-1-[4-(2-hydroxy-ethylamino)-phenyl]-pent-4-en-1-one are dissolved in 55 ml THF and 137 ml acetonitrile. 4.5 ml (60 mmol) of a 37% aqueous formaldehyde solution are added over 10 min. at 25° C., followed by 2.21 g (30 mmol) of sodium cyanoborohydride. After 10 min at 25° C., the mixture is stirred at 50° C. for 4 h, cooled to room temperature and diluted with 100 ml water. The yellow semi-solid is redissolved in methylene chloride, washed with 20 ml of aq. sat. NaHCO3 and water, the organic phase dried with brine and sodium sulfate, and evaporated under vacuum to give 2.3 g (75%) of the title compound as a yellow oil.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with 20 ml of aq. sat. NaHCO3 and water
  3. dry with materialthe organic phase dried with brine and sodium sulfate
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-97f77af54d1447dea9b94ddf142dbbb6
Source dataset
uspto-grants-2010_06
Patent number
US07732504B2

Reaction notes

Loading…