Dichloromethane → Ammonia dichloromethane

HRID 33713Notes

Reaction equation

HRID 33713 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:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27][CH2:26]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]>>[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[CH2:24][CH2:23][CH:22]([N:25]4[C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[CH2:27][CH2:26]4)[CH2:21][CH2:20]3)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 27663244-(3-Piperidin-1-ylpropoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 220286031-Piperidin-4-yl-2,3-dihydro-1H-indole

Product 2

HCID 101600051-{1-[4-(3-Piperidin-1-yl-propoxy)-benzyl]-piperidin-4-yl}-2,3-dihydro-1H-indoleHCID 22731429Ammonia dichloromethaneYield 1%

Procedure

A solution of the product of Example 9 (112 mg) and 1-piperidin-4-yl-2,3-dihydro-1H-indole*2TFA (194 mg) in DCM (2 mL) was treated with sodium triacetoxyborohydride (150 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 (78 mg). 1H NMR (400 MHz, CDCl3): 7.22 (d, J=8.6 Hz, 2H), 7.06-7.00 (m, 2H), 6.85 (d, J=8.6 Hz, 2H), 6.59 (t, J=7.1 Hz, 1H), 6.39(d, J=7.8 Hz, 1H), 4.00 (t, J=6.3 Hz, 2H), 3.48 (s, 2H), 3.41-3.32 (m, 3H), 2.99 (m, 2H), 2.93 (t, J=8.3 Hz, 2H), 2.54 (m, 2H), 2.47 (br, 4H), 2.09-1.98 (m, 4H), 1.79-1.70 (m, 4H), 1.67-1.61 (m, 4H), 1.50-1.43 (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-23a60376338448c6997bd5f660fac75d
Source dataset
uspto-grants-2008_09
Patent number
US07429586B2

Reaction notes

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