Hydrochloric Acid → HCID 67573467, compound

HRID 399045Notes

Reaction equation

HRID 399045 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:23])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])=[CH:11][CH:10]=1.C(N(CC)CC)C.Cl[C:32]([O:34][CH2:35][CH3:36])=[O:33].Cl>C(OCC)C>[CH2:35]([O:34][C:32]([NH:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([CH3:23])([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH3:16])=[CH:13][CH:14]=1)=[O:33])[CH3:36]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 67573807HCID 67573807, compound

Product 1

HCID 67573467HCID 67573467, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of (±) cis-1-amino-2-[4-(1-methyl-1-phenylethyl)phenoxymethyl] cyclopentane (0.35 g, 1.13 mmol) in dry diethyl ether (30 ml) containing triethylamine (0.31 ml, 2.26 mmol) was added a solution of ethyl chloroformate (0.18 g, 1.70 mmol) in diethyl ether (5 ml). The reaction was stirred at room temperature for 2 h and then poured into ice-water. The pH of the aqueous phase was adjusted to approximately 7 by the addition of dilute hydrochloric acid. The aqueous layer was separated and extracted with diethyl ether (2×30 ml). The combined organic layers were washed with water followed by brine, then dried over sodium sulfate and concentrated in vacuo to give an oil (0.41 g) which was used in the next stage without purification.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with diethyl ether (2×30 ml)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d867e2fdbf594cc1b9e3d464e6f84ac3
Source dataset
uspto-grants-1998_10
Patent number
US05817698

Reaction notes

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