Dichloromethane → Ammonia dichloromethane

HRID 33718

Reaction equation

HRID 33718 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][N:17]1[CH2:22][CH2:23][CH2:24]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C.[CH2:61]([Cl:63])[Cl:62]>>[NH3:1].[CH2:61]([Cl:63])[Cl:62].[CH3:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][N:17]1[CH2:22][CH2:23][CH2:24][O:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:13][CH:12]=1

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 2488061-Piperidinepropanol, 2-methyl-HCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 116369724-Piperidin-1-ylmethyl-phenol

Product 2

HCID 99454132-Methyl-1-[3-(4-piperidin-1-ylmethyl-phenoxy)-propyl]-piperidineHCID 22731429Ammonia dichloromethaneYield 2.5%

Procedure

A suspension of the product of Example 17 (176 mg), 3-(2-methyl-piperidin-1-yl)-propan-1-ol (145 mg), and polymer supported triphenylphosphine (613 mg; loading: 3 mmol/g) in DCM (5 mL) was treated with di-tert-butylazodicarboxylate (316 mg). After 2 h, the resulting mixture was filtered, and the filtrate was evaporated. Chromatography of the residue (2.5% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (60 mg). 1H NMR (400 MHz, CDCl3): 7.20 (d, J=8.6 Hz, 2H), 6.83 (d, J=8.6 Hz, 2H), 4.01-3.92 (m, 2H), 3.40 (s, 2H), 2.90-2.81 (m, 2H), 2.56-2.47 (m, 1H), 2.40-2.25 (m, 5H), 2.21-2.14 (m, 1H), 1.97-1.88 (m, 2H), 1.70-1.51 (m, 8H), 1.45-1.25 (m, 4H), 1.07 (d, J=6.2 Hz, 3H).

Workup

  1. filtrationthe resulting mixture was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-f4f114e9b4ef4aaebd94bc79e175298e
Source dataset
uspto-grants-2008_09
Patent number
US07429586B2

Linked notes

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