Dichloromethane → Ammonia dichloromethane

HRID 33731Notes

Reaction equation

HRID 33731 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]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)([CH3:21])[CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].[CH2:44]([Cl:46])[Cl:45]>C(O)(=O)C>[NH3:1].[CH2:44]([Cl:46])[Cl:45].[CH:19]([N:22]1[CH2:27][CH2:26][N:25]([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)[CH2:24][CH2:23]1)([CH3:21])[CH3:20]

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 780131-IsopropylpiperazineHCID 27663244-(3-Piperidin-1-ylpropoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 2

HCID 101554031-Isopropyl-4-[4-(3-piperidin-1-yl-propoxy)-benzyl]-piperazineHCID 22731429Ammonia dichloromethaneYield 1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the product of Example 9 (200 mg), 1-isopropyl-piperazine (100 mg), and acetic acid (0.05 mL) in DCM (3 mL) was treated with sodium triacetoxyborohydride (290 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 (225 mg). 1H NMR (400 MHz, CDCl3): 7.19 (d, J=8.6 Hz, 2H), 6.83 (d, J=8.6 Hz, 2H), 3.98 (t, J=6.6 Hz, 2H), 3.43 (s, 2H), 2.63 (m, 1H), 2.53 (br, 4H), 2.46 (m, 4H), 2.39 (br, 4H), 1.96 (m, 2H), 1.58 (m, 4H), 1.46-1.40 (m, 2H), 1.03 (d, J=6.5 Hz, 6H).

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-59ed4c5836a74af7b0dc4532aaac0233
Source dataset
uspto-grants-2008_09
Patent number
US07429586B2

Reaction notes

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