Dichloromethane → Ammonia dichloromethane

HRID 33703Notes

Reaction equation

HRID 33703 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]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)[CH2:26][CH2:27][N:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].[CH2:55]([Cl:57])[Cl:56]>C(O)(=O)C>[NH3:1].[CH2:55]([Cl:57])[Cl:56].[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[CH2:24][CH2:23][CH:22]([N:25]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=4)[CH2:26][CH2:27][N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)[CH2:21][CH2:20]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 5049666Sodium triacetoxyborohydrideHCID 17962599Piperidin-4-yl-pyridin-2-yl-(2-pyrrolidin-1-yl-ethyl)-amine

Product 2

HCID 10278949{1-[4-(3-Piperidin-1-yl-propoxy)-benzyl]-piperidin-4-yl}-pyridin-2-yl-(2-pyrrolidin-1-yl-ethyl)-amineHCID 22731429Ammonia dichloromethaneYield 1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the product of Example 9 (30 mg), piperidin-4-yl-pyridin-2-yl-(2-pyrrolidin-1-yl-ethyl)-amine (29.8 mg), and acetic acid (0.015 mL) in DCM (1 mL) was treated with sodium triacetoxyborohydride (38 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 (sodium sulfate) and evaporated. Chromatography of the residue (1-10% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (26 mg). 1H NMR (400 MHz, CDCl3): 8.12 (m, 1H), 7.39 (m, 1H), 7.21 (d, J=8.6 Hz, 2H), 6.85 (d, J=8.6 Hz, 2H), 6.53-6.47 (m, 2H), 4.44 (m, 1H), 3.99 (t, J=6.3 Hz, 2H), 3.51-3.47 (m, 2H), 3.46 (s, 2H), 2.95 (m, 2H), 2.62 (m, 6H), 2.49 (m, 2H), 2.42 (m, 4H), 2.12 (m, 2H), 1.98 (m, 2H), 1.84-1.78 (m, 5H), 1.75 (m, 1H), 1.68 (m, 2H), 1.63-1.57 (m, 4H), 1.44 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-4cba649a98e048f38d0b666d4e13cb13
Source dataset
uspto-grants-2008_09
Patent number
US07429586B2

Reaction notes

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