4-(4-Chlorophenyl)-4-hydroxypiperidine → HCID 67300004, compound

HRID 1016109Notes

Reaction equation

HRID 1016109 reaction equation
[C:1]([NH:9][C@H:10]([C:14]([OH:16])=O)[C@@H:11]([CH3:13])O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]2([OH:49])[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)=[CH:39][CH:38]=1>CO.ClCCCl.CN(C=O)C>[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]2([OH:49])[CH2:44][CH2:45][N:46]([C:14](=[O:16])[C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:11][CH3:13])[CH2:47][CH2:48]2)=[CH:39][CH:38]=1

Participants

8

Reactant 4

HCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 736177N-Benzoylthreonine

Product 1

HCID 67300004HCID 67300004, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolvent2×HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A reaction vessel was charged with N-benzoyl-L-threonine (56 mg), HOBt (42 mg), DIEA (130 μL), 4-(4-chlorophenyl)-4-hydroxypiperidine (66 mg), EDC (60 mg), DMF (1 mL) and 1,2-dichloroethane (1 mL). The reaction mixture was stirred for 16 h at rt and then diluted with methanol (0.5 mL). Upon completion of dilution, the reaction mixture was purified by preparative LC-MS to provide Example 226. MS found: (M+H)+=399.

Workup

  1. customUpon completion of dilution, the reaction mixture was purified by preparative LC-MS
  2. customto provide Example 226

Sources & evidence

ORD record
ord-5bd172a1efe24b3ea9d406e1335b8543
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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