1,2-Dichloroethane → Ammonia dichloromethane

HRID 33708Notes

Reaction equation

HRID 33708 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.[ClH:19].[CH3:20][NH:21][CH3:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].ClC[CH2:41][Cl:42]>C(O)(=O)C>[NH3:1].[CH2:41]([Cl:42])[Cl:19].[CH3:20][N:21]([CH3:22])[CH2:15][C:14]1[CH:17]=[CH:18][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:12][CH:13]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 10473Dimethylamine, hydrochlorideHCID 14798Sodium HydroxideHCID 27663244-(3-Piperidin-1-ylpropoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 2

HCID 9835304Dimethyl-[4-(3-piperidin-1-yl-propoxy)-benzyl]-amineHCID 22731429Ammonia dichloromethaneYield 3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the product of Example 9 (175 mg), dimethylamine hydrochloride (64 mg), and acetic acid (0.05 mL) in DCE (3 mL) was treated with sodium triacetoxyborohydride (210 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (1 mL) and extracted with DCM (3×3 mL). The combined organic phases were dried (magnesium sulfate) and evaporated. Chromatography of the residue (3% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (70 mg). 1H NMR (400 MHz, CDCl3): 7.19 (d, J=8.6 Hz, 2H), 6.85 (d, J=8.6 Hz, 2H), 3.99 (t, J=6.4 Hz, 2H), 3.35 (s, 2H), 2.50-2.35 (m, 6H), 2.22 (s, 6H), 2.01-1.94 (m, 2H), 1.63-1.55 (m, 4H), 1.46-1.40 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-6997b950122f4a9b92b87a8a9051f427
Source dataset
uspto-grants-2008_09
Patent number
US07429586B2

Reaction notes

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