1,2-Dichloroethane → Ammonia dichloromethane

HRID 33728Notes

Reaction equation

HRID 33728 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].[Cl:43]CCCl>C(O)(=O)C>[NH3:1].[CH2:20]([Cl:19])[Cl:43].[Cl:19][C:20]1[CH:26]=[CH:25][C:23]([NH:24][CH2:15][C:14]2[CH:17]=[CH:18][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:12][CH:13]=2)=[CH:22][CH:21]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 78124-ChloroanilineHCID 14798Sodium HydroxideHCID 27663244-(3-Piperidin-1-ylpropoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 2

HCID 9924984HCID 9924984, compoundHCID 22731429Ammonia dichloromethaneYield 1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the product of Example 9 (260 mg), 4-chloroaniline (180 mg), and acetic acid (0.06 mL) in DCE (3 mL) was treated with sodium triacetoxyborohydride (360 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (5 mL) and extracted with DCM (3×10 mL). The combined organic phases were dried (sodium sulfate) and evaporated. Chromatography of the residue (1-5% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (168 mg). 1H NMR (400 MHz, CDCl3): 7.25 (d, J=8.8 Hz, 2H), 7.10 (d, J=8.9 Hz, 2H), 6.87 (d, J=8.8 Hz, 2H), 6.54 (d, J=8.9 Hz, 2H), 4.21 (d, J=4.7, 2H), 3.99 (t, J=6.3 Hz, 2H), 2.52-2.38 (m, 6H), 1.99 (m, 2H), 1.64-1.57 (m, 4H), 1.49-1.42 (m, 2H).

Workup

  1. extractionextracted with DCM (3×10 mL)
  2. dry with materialThe combined organic phases were dried (sodium sulfate)
  3. customevaporated

Sources & evidence

ORD record
ord-983eb3aa4ba141ccba09272c42ec4c12
Source dataset
uspto-grants-2008_09
Patent number
US07429586B2

Reaction notes

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