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Dichloromethane → Ammonia dichloromethane

HRID 33723
Notes
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Reaction equation

HRID 33723 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.[CH2:19]([NH:26][CH3:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.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].[CH2:19]([N:26]([CH3:27])[CH2:15][C:14]1[CH:17]=[CH:18][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:12][CH:13]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 7669N-MethylbenzylamineHCID 14798Sodium HydroxideHCID 27663244-(3-Piperidin-1-ylpropoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 2

HCID 10291629Benzyl-methyl-[4-(3-piperidin-1-yl-propoxy)-benzyl]-amine
HCID 22731429Ammonia dichloromethaneYield 1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the product of Example 9 (218 mg), benzyl methylamine (108 mg), and acetic acid (0.05 mL) in DCM (3 mL) was treated with sodium triacetoxyborohydride (300 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 (269 mg). 1H NMR (400 MHz, CDCl3): 7.37-7.28 (m, 4H), 7.27-7.22 (m, 5H), 6.85 (d, J=8.6 Hz, 2H), 3.99 (t, J=6.3 Hz, 2H), 3.49 (s, 2H), 3.45 (s, 2H), 2.50-2.31 (m, 6H), 2.16 (s, 3H), 1.97 (m, 2H), 1.62-1.55 (m, 4H), 1.47-1.40 (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-23041234c67b40b7b295c2daace6f109
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07429586B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes