Dichloromethane → Ammonia dichloromethane

HRID 33706Notes

Reaction equation

HRID 33706 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.[CH3:19][N:20]([CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].[CH2:51]([Cl:53])[Cl:52]>C(O)(=O)C>[NH3:1].[CH2:51]([Cl:53])[Cl:52].[CH3:19][N:20]([CH2:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH:21]1[CH2:22][CH2:23][N: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)[CH2:25][CH2:26]1

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 27663244-(3-Piperidin-1-ylpropoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 10856966Methyl-phenethyl-piperidin-4-YL-amine

Product 2

HCID 10204231Methyl-phenethyl-{1-[4-(3-piperidin-1-yl-propoxy)-benzyl]-piperidin-4-yl}-amineHCID 22731429Ammonia dichloromethaneYield 1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the product of Example 9 (152 mg), methyl-phenethyl-piperidin-4-yl-amine (128 mg), and acetic acid (0.11 mL) in DCM (3 mL) was treated with sodium triacetoxyborohydride (190 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 (148 mg). 1H NMR (400 MHz, CDCl3): 7.29-7.25 (m, 2H), 7.21-7.16 (m, 5H), 6.83 (j, J=8.6 Hz, 2H), 3.99 (d, J=6.3 Hz, 2H), 3.41 (s, 2H), 2.92 (m, 2H), 2.77-2.66 (m, 4H), 2.47 (m, 2H), 2.40 (m, 4H), 2.34 (s, 3H), 2.00-1.88 (m, 4H), 1.71 (m, 2H), 1.62-1.55 (m, 6H), 1.44 (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-189cbcb15532405e8f223b2e49595325
Source dataset
uspto-grants-2008_09
Patent number
US07429586B2

Reaction notes

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