Dichloromethane → Ammonia dichloromethane

HRID 33715Notes

Reaction equation

HRID 33715 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=2[CH:13]=O)[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+].[CH2:43]([Cl:45])[Cl:44]>C(O)(=O)C>[NH3:1].[CH2:43]([Cl:45])[Cl:44].[Cl:19][C:20]1[CH:26]=[CH:25][C:23]([NH:24][CH2:13][C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[O:10][CH2:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:22][CH:21]=1

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 78124-ChloroanilineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 137952592-[3-(1-Piperidinyl)propoxy]benzaldehyde

Product 2

HCID 17962633(4-Chloro-phenyl)-[2-(3-piperidin-1-yl-propoxy)-benzyl]-amineHCID 22731429Ammonia dichloromethaneYield 1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-(3-piperidin-1-yl-propoxy)-benzaldehyde (266 mg), 4-chloroaniline (146 mg), and acetic acid (0.07 mL) in DCM (5 mL) was treated with sodium triacetoxyborohydride (400 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (6 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 (246 mg). 1H NMR (400 MHz, CDCl3): 7.28-7.20 (m, 2H), 7.09 (d, J=8.9 Hz, 2H), 6.89 (m, 2H), 6.55 (d, J=8.9 Hz, 2H), 4.30 (d, J=5.6, 2H), 4.18 (m, 1H), 4.05 (t, J=6.3 Hz, 2H), 2.47 (m, 2H), 2.37 (br, 4H), 1.96 (m, 2H), 1.62-1.56 (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-044f9b8c9d104eddb09c316417fbb2a6
Source dataset
uspto-grants-2008_09
Patent number
US07429586B2

Reaction notes

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