Ammonia → 3-phenoxypiperidine

HRID 1647523Notes

Reaction equation

HRID 1647523 reaction equation
[NH2:1][N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3]1.C([O:23][C@@H:24]1[C@H:28]([O:29]C(=O)C2C=CC=CC=2)[C@@H:27]([CH2:38][O:39]C(=O)C2C=CC=CC=2)[O:26][C@H:25]1[N:48]1[CH:56]=[N:55][C:54]2[C:49]1=[N:50][C:51]([Cl:58])=[N:52][C:53]=2Cl)(=O)C1C=CC=CC=1.N>>[Cl:58][C:51]1[N:52]=[C:53]([NH:1][N:2]2[CH2:7][CH2:6][CH2:5][CH:4]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:3]2)[C:54]2[N:55]=[CH:56][N:48]([C:49]=2[N:50]=1)[C@@H:25]1[O:26][C@H:27]([CH2:38][OH:39])[C@@H:28]([OH:29])[C@H:24]1[OH:23].[O:8]([CH:4]1[CH2:5][CH2:6][CH2:7][NH:2][CH2:3]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purineHCID 23367727HCID 23367727, compound

Product 2

HCID 37305813-phenoxypiperidineYield 215.7%HCID 44323017HCID 44323017, compound

Procedure

2-Chloro-N-(3-phenoxy-1-piperidinyl)adenosine was prepared according to method A as described in Example 6 by reacting 1-amino-3-phenoxypiperidine (0.60 g, 3.4 mmol) with 9-(2',3',5'tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.0 g, 3.2 mmol), followed by debenzoylation of the purified product using methanolic ammonia. This provided the desired compound (0.65 g, 43%) (after column chromatography) as a foam, 1H NMR (DMSO-d6) δ3.53-3.60 (1H, m, H-5'), 3.64-3.72 (1H, m, H-5'b), 3.96 (1H, q, H-4'), 4.14 (1H, q, H-3'), 4.50-4.59 (1H, m, H-2' and --C--H)), 5.07 (1H, t, 5'-OH), 5.23, 5.50 (2H, 2d, 2'- and 3'-OH), 5.84 (1H, d, H-1'), 6.79-7.32 (5H, 3m, Ar-H), 8.45 (1H, s, H-8), 9.55 (1H, s, N--H).

Sources & evidence

ORD record
ord-c85147fe20d84190932907f58dc1f153
Source dataset
uspto-grants-1995_07
Patent number
US05432164

Reaction notes

Loading…