Carbamate → HCID 2729115, compound

HRID 618454Notes

Reaction equation

HRID 618454 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22].[CH2:23]([NH2:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].[C:30](=[O:33])([O-])N.[C:34]([O:38]C)(C)(C)C>C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:30](=[O:33])[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:34](=[O:38])[NH:29][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 276CarbamateHCID 8102HexylamineHCID 15413tert-Butyl methyl etherHCID 199606-Amino-1-hexanolHCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 2729115HCID 2729115, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

A stirred suspension of N,N'-carbonyldiimidazole (58.38 g, 0.36 mol) in methylene chloride (250 mL) was treated with a solution of 1-benzyl-4-hydroxypiperidine (57.80 g, 0.30 mol) in the same solvent (200 mL) at RT. The resulting clear solution was stirred for 2 hrs., washed 3 times with water (60 mL), and the organic phase was added into a solution of 6 -aminohexanol (52.8 g, 0.45 mol) in methylene chloride (150 mL). The reaction mixture was kept overnight at RT, washed with water, dried over magnesium sulfate, filtered, and concentrated. Comparative TLC confirmed that the product was identical to the intermediate carbamate prepared according to Example 1. The material was redissolved in methylene chloride (110 mL) and added to a stirred suspension of N,N'-carbonyldiimidazole (53.50 g, 0.33 mol) in the same solvent (250 mL). The resulting solution was kept for 1 hr. at RT, and then mixed with a solution of hexylamine (60 mL, approx. 1.5 eq.) in methylene chloride (60 mL). The reaction mixture was stirred overnight at RT, washed with water, dried over magnesium sulfate, filtered, and evaporated to give waxy, semi-solid residue. The contents of the flask were slurried in t-butyl-methyl ether (200 mL) and the first crop of crystals collected by filtration. Another crop of crystalline product was obtained upon addition of heptane to the filtrate. The product (111.95 g, 80%), m.p. 78-80° C., was identical with the carbamate prepared according to Example 2.

Workup

  1. wash, washed 3 times with water (60 mL)
  2. waitThe reaction mixture was kept overnight at RT
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customprepared
  8. waitThe resulting solution was kept for 1 hr
  9. stirringThe reaction mixture was stirred overnight at RT
  10. washwashed with water
  11. dry with materialdried over magnesium sulfate
  12. filtrationfiltered
  13. customevaporated
  14. customto give waxy, semi-solid residue
  15. filtrationthe first crop of crystals collected by filtration
  16. customAnother crop of crystalline product was obtained upon addition of heptane to the filtrate
  17. customprepared

Sources & evidence

ORD record
ord-aeb5d238aad246f2a01b8e835f2bcfa7
Source dataset
uspto-grants-1999_09
Patent number
US05952506

Reaction notes

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