Aniline → Ammonia dichloromethane

HRID 456951Notes

Reaction equation

HRID 456951 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.[NH2:19][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+].[CH2:42]([Cl:44])[Cl:43]>C(O)(=O)C>[NH3:1].[CH2:42]([Cl:44])[Cl:43].[C:20]1([NH:19][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)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 5

HCID 6115AnilineHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 27663244-(3-Piperidin-1-ylpropoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 2

HCID 9945134Phenyl-[4-(3-piperidin-1-yl-propoxy)-benzyl]-amineHCID 22731429Ammonia dichloromethaneYield 1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the product of Example 9 (277 mg), aniline (108 mg), and acetic acid (0.07 mL) in DCM (5 mL) was treated with sodium triacetoxyborohydride (340 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (10 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 (256 mg). 1H NMR (400 MHz, CDCl3): 7.27 (m, 2H), 7.18 (m, 2H), 6.88 (m, 2H), 6.72 (m, 2H), 6.64 (m, 2H), 4.24 (s, 2H), 4.00 (t, J=6.6 Hz, 2H), 3.94 (br, 1H), 2.48 (m, 2H), 2.41 (br, 4H), 1.98 (m, 2H), 1.64–1.57 (m, 4H), 1.48–1.41 (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-941059cbc95e4b48a63c1718dab27ebf
Source dataset
uspto-grants-2007_03
Patent number
US07186732B2

Reaction notes

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