Dichloromethane → Ammonia dichloromethane

HRID 33717Notes

Reaction equation

HRID 33717 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.[CH:19](=[C:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].[CH2:48]([Cl:50])[Cl:49]>C(O)(=O)C>[NH3:1].[CH2:48]([Cl:50])[Cl:49].[CH:19](=[C:26]1[CH2:31][CH2:30][N:29]([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)[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 27663244-(3-Piperidin-1-ylpropoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 107735594-Benzylidene-piperidine

Product 2

HCID 102229151-{3-[4-(4-Benzylidene-piperidin-1-ylmethyl)-phenoxy]-propyl}-piperidineHCID 22731429Ammonia dichloromethaneYield 1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the product of Example 9 (204 mg), 4-Benzylidene-piperidine (145 mg), and acetic acid (0.05 mL) in DCM (3 mL) was treated with sodium triacetoxyborohydride (300 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 (magnesium sulfate) and evaporated. Chromatography of the residue (1 to 5% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (308 mg). 1H NMR (400 MHz, CDCl3): 7.30 (m, 2H), 7.24-7.16 (m, 4H), 6.84 (m, 2H), 6.26 (s, 1H), 3.99 (t, J=6.3 Hz, 2H), 3.46 (s, 2H), 2.54-2.44 (m, 6H), 2.43-2.35 (m, 6H), 1.97 (m, 2H), 1.74 (br, 1H), 1.63-1.56 (m, 4H), 1.47-1.40 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-5158fd3ccb9d453d8dd2bbc44258e5c3
Source dataset
uspto-grants-2008_09
Patent number
US07429586B2

Reaction notes

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