Ammonium Chloride → HCID 178523299, compound

HRID 1829675Notes

Reaction equation

HRID 1829675 reaction equation
[CH2:1]([O:8][C:9](=[O:27])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][C:25]#[N:26])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:28]=[N+:29]=[N-:30].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:27])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][C:25]2[NH:30][N:29]=[N:28][N:26]=2)=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 21031122HCID 21031122, compound

Product 1

HCID 178523299HCID 178523299, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of {4-[4-(3-cyanopropoxy)phenyl]butyl}carbamic acid benzyl ester 2 (0.90 g, 2.5 mmol), sodium azide (0.50 g, 7.5 mmol), and ammonium chloride (0.40 g, 7.5 mmol) in DMF (7 mL), was stirred at 120° C. for 16 h. Inorganics were removed by vacuum filtration. The filtrate was diluted with ethyl acetate, and washed with water and brine. The organic solution was dried over Na2SO4, filtered and concentrated. The residue was taken up in ethyl acetate (5 mL) and diluted with hexanes (10 mL). Solid precipitates were collected by suction filtration and purified by flash silica gel column chromatography eluting with methanol/dichloromethane (1:50, v/v) to give the desired product 3 as a white solid (0.78 g, 76% yield). 1H NMR (300 MHz, CD3OD) δ 1.51 (m, 4H), 2.20 (m, 2H), 2.50 (m, 2H), 3.10 (m, 4H), 4.00 (m, 2H), 5.00 (s, 2H), 6.75 (d, 2H), 7.05 (d, 2H), 7.30 (m, 5H). m/z (ESI): 410 [C22H27N5O3+H]+.

Workup

  1. customInorganics were removed by vacuum filtration
  2. additionThe filtrate was diluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic solution was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additiondiluted with hexanes (10 mL)
  8. customSolid precipitates
  9. filtrationwere collected by suction filtration
  10. custompurified by flash silica gel column chromatography
  11. washeluting with methanol/dichloromethane (1:50

Sources & evidence

ORD record
ord-b64c4d31e64843a38ca392741755d541
Source dataset
uspto-grants-2006_06
Patent number
US07064129B2

Reaction notes

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