Dichloromethane → Ammonia dichloromethane

HRID 33724

Reaction equation

HRID 33724 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.[CH2:15]([N:17]([CH2:21][CH3:22])[CH2:18][CH2:19]O)[CH3:16].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.[CH2:58]([Cl:60])[Cl:59]>>[NH3:1].[CH2:58]([Cl:60])[Cl:59].[CH2:15]([N:17]([CH2:21][CH3:22])[CH2:18][CH2:19][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)[CH3:16]

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 7497DiethylethanolamineHCID 11776TriphenylphosphineHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 116369724-Piperidin-1-ylmethyl-phenol

Product 2

HCID 11808427Diethyl-[2-(4-piperidin-1-ylmethyl-phenoxy)-ethyl]-amineHCID 22731429Ammonia dichloromethaneYield 3%

Procedure

A suspension of the product of Example 17 (176 mg), 2-Diethylamino-ethanol (0.12 mL), 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 (3% 2 M methanolic ammonia/DCM) gave the title compound as a pale yellow oil (37 mg). 1H NMR (400 MHz, CDCl3): 7.20 (d, J=8.8 Hz, 2H), 6.84 (d, J=8.6 Hz, 2H), 4.03 (t, J=6.5 Hz, 2H), 3.40 (s, 2H), 2.87 (t, J=6.5 Hz, 2H), 2.63 (q, J=7.0 Hz, 4H), 2.35 (br s, 4H), 1.59-1.52 (m, 4H), 1.46-1.37 (m, 2H), 1.07 (t, J=7.1 Hz, 6H).

Workup

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

Sources & evidence

ORD record
ord-9009b5b4fb8d4ce49b26ebb66249c190
Source dataset
uspto-grants-2008_09
Patent number
US07429586B2

Linked notes

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