Hydrogen Bromide → HCID 178511510, compound

HRID 25650

Reaction equation

HRID 25650 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][Br:19])[CH2:10][CH2:9]1)(C)(C)C.CO.Br.C(Br)(=O)C>C1(C)C=CC=CC=1>[Br:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C@H:11]1[CH2:10][CH2:9][C@H:8]([NH2:7])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 887Methanol2×HCID 10482Acetyl bromideHCID 178453880HCID 178453880, compound

Product 1

HCID 178511510HCID 178511510, compoundYield 129.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

At 0° C., a solution of 4.4 g (12.63 mmol) of trans-[4-(5-Bromo-pentyl)-cyclohexyl]-carbamic acid tert-butyl ester were received in 9 m MeOH was added to 40 ml of a HBr solution in MeOH (made by dropping at 0° C., 4.7 ml (63.07 mmol) of acetylbromide to 35 ml MeOH). The suspension was stirred for 16 h at RT, diluted with toluene and evaporated (2×). The residue was suspended in EtOAc (40 ml) cooled (−10 to −15° C.) and filtered to give 4.05 g (97%) of trans-4-(5-Bromo-pentyl)-cyclohexylamine as hydrobromide salt, MS: 248 (MH+, 1Br).

Workup

  1. customAt 0° C.
  2. customevaporated (2×)
  3. temperaturecooled (−10 to −15° C.)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-22ce0e8d65a6428bb6e10a3a78ceabba
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Linked notes

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