Hydrochloric Acid → HCID 22452686, compound

HRID 2185912Notes

Reaction equation

HRID 2185912 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH2:18][NH2:19])[CH2:15][CH2:16][OH:17])=[CH:10][CH:9]=1.C(N(CC)CC)C.Cl>C(Cl)Cl>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]([CH2:18][NH:19][C:2]([O:4][CH2:5][CH3:6])=[O:3])[CH2:15][CH2:16][OH:17])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 22452659HCID 22452659, compound

Product 1

HCID 22452686HCID 22452686, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chloroformate (4.7 mL, 49.5 mmol) was added dropwise to a stirred cooled (−40° C.) solution of 3-(4-chlorophenyl)-4-amino-1-butanol (9.0 g, 45 mmol) and triethylamine (7.2 mL, 51.8 mmol) in DCM (125 mL). The solution was stirred at room temperature for 30 min and poured into 1N HCl (60 mL). The organic layer was washed with 1N HCl (70 mL), saturated sodium bicarbonate (70 mL) and saturated sodium chloride; dried (MgSO4), filtered and the solvent removed to provide the title compound (11.4 g, 93%) as a yellow oil. 1H-NMR (CDCl3): δ 1.18-1.23 (t, 3H CH) 1.75-1.84 (m, 1H, CH) 1.90-1.99 (m, 1H, CH) 2.94-2.99 (m, 1H, CH) 3.21-3.30 (m, 1H, CH) 3.47-3.65 (m, 3H, CH) 4.04-4.11 (q, 2H, CH) 4.58 (s, 1H, OH or NH) 7.12-7.15 (d, 2R, ArH) 7.26-7.37 (m, 2H, ArH); MS m/z 272 (M+H).

Workup

  1. washThe organic layer was washed with 1N HCl (70 mL), saturated sodium bicarbonate (70 mL) and saturated sodium chloride
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent removed

Sources & evidence

ORD record
ord-9b05e054aa1c40d08950d58d4f2984a2
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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