Dichloromethane → HCID 25122571, compound

HRID 1296223Notes

Reaction equation

HRID 1296223 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1([C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([OH:17])=O)[OH:11])[CH3:3].C(Cl)Cl.[CH2:24]([NH:26][CH2:27][CH3:28])[CH3:25].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O>[CH3:3][N:2]([CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1([C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([N:26]([CH2:27][CH3:28])[CH2:24][CH3:25])=[O:17])[OH:11])[CH3:1]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8021DiethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69469447HCID 69469447, compound

Product 1

HCID 25122571HCID 25122571, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A sample of 3-[(1-RS,2-RS)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-benzoic acid (0.1 g, 0.36 mmol), CH2Cl2 (5 mL), and diethylamine (0.08 mL, 0.36 mmol) was placed into a flask and stirred for 5 min. To the reaction was added HATU (0.13 g, 0.36 mmol) and stirring was continued for 2 h. Water was added and the organic phase was separated, washed again with water, dried (Na2SO4), and filtered. The filtrate was evaporated in vacuo and the residue passed through a silica gel column (90:10:1, CH2Cl2:MeOH:NH4OH) to give 42 mg (35%) of 3-[(1-RS,2-RS)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-N,N-diethyl-benzamide: MS m/z=333 (MH+); 1H NMR (CDCl3) δ 7.7-7.2 (Ar, 4H), 3.6 and 3.2 (bq, 4H), 2.4 (dd, 1H), 2.1 (s, 6H), 2.0-1.5 (m, 10H), 1.1 (bt, 6H).

Workup

  1. stirringstirring
  2. waitwas continued for 2 h
  3. customthe organic phase was separated
  4. washwashed again with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-d6867f829ec7450791e54193aa247ff5
Source dataset
uspto-grants-2007_07
Patent number
US07244866B2

Reaction notes

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