Dichloromethane → Ammonia dichloromethane

HRID 33709Notes

Reaction equation

HRID 33709 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.[NH:19]1[CH2:24][CH2:23][CH:22]([N:25]2[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[N:27]=[CH:26]2)[CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].[CH2:50]([Cl:52])[Cl:51]>C(O)(=O)C>[NH3:1].[CH2:50]([Cl:52])[Cl:51].[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH2:15][N:19]3[CH2:20][CH2:21][CH:22]([N:25]4[C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=5[N:27]=[CH:26]4)[CH2:23][CH2:24]3)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 27663244-(3-Piperidin-1-ylpropoxy)benzaldehydeHCID 30192621-(4-Piperidinyl)-1H-benzimidazoleHCID 5049666Sodium triacetoxyborohydride

Product 2

HCID 101599471-{1-[4-(3-Piperidin-1-yl-propoxy)-benzyl]-piperidin-4-yl}-1H-benzoimidazoleHCID 22731429Ammonia dichloromethaneYield 1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the product of Example 9 (82 mg), 1-Piperidin-4-yl-1H-benzoimidazole (62 mg), and acetic acid (0.03 mL) in DCM (3 mL) was treated with sodium triacetoxyborohydride (110 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 (81 mg). 1H NMR (400 MHz, CDCl3): 7.98 (s, 1H), 7.80 (m, 1H), 7.42 (m, 1H), 7.30-7.20 (m, 4H), 6.87 (d, J=8.6 Hz, 2H), 4.18 (m, 1H), 4.00 (t, J=6.3 Hz, 2H), 3.52 (s, 2H), 3.10-3.03 (m, 2H), 2.48 (m, 2H), 2.41 (br, 4H), 2.21-2.10 (m, 5H), 2.01-1.94 (m, 2H), 1.62-1.55 (m, 4H), 1.47-1.39 (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-754138a0ac244b37a90016f926498ac1
Source dataset
uspto-grants-2008_09
Patent number
US07429586B2

Reaction notes

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