Hydrochloric Acid → HCID 22763944, compound

HRID 1112398Notes

Reaction equation

HRID 1112398 reaction equation
Br[C:2]12[CH2:11][C:6]3([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:7][CH:8]([CH2:10][C:4]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:5]3)[CH2:3]1)[CH2:9]2.[NH2:20]C(N)=O.[ClH:24]>O>[ClH:24].[NH2:20][C:2]12[CH2:11][C:6]3([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:7][CH:8]([CH2:10][C:4]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:5]3)[CH2:3]1)[CH2:9]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1176UreaHCID 15529888HCID 15529888, compound

Product 1

HCID 22763944HCID 22763944, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3.27 grams of 1-bromo-3,5-di-n-butyl-adamantane were warmed with 1.2 grams of urea for 160 minutes at 165° C. The heating was performed in a closed vessel in a thermostatically controlled oil bath. After cooling, the reaction product was suspended in 50 ml. water. The water phase was brought to a pH of about 4 through dropwise addition of concentrated hydrochloric acid. The water phase was then extracted with two 10-ml. portions of ether, and brought to a pH of about 13 by dropwise addition of sodium hydroxide. The alkaline solution was stirred for about 10 minutes, after which the aqueous alkaline phase was extracted with four 10-ml. portions of benzene. The combined benzene extracts were dried over fused potassium sulfate. 1-amino-3,5-di-n-butyl-adamantane hydrochloride was precipitated by exposure to dried hydrogen chloride gas. Yield: 1.86 grams (62% of the theoretical yeild).

Workup

  1. customThe heating was performed in a closed vessel in a thermostatically controlled oil bath
  2. temperatureAfter cooling
  3. extractionThe water phase was then extracted with two 10-ml
  4. additionportions of ether, and brought to a pH of about 13 by dropwise addition of sodium hydroxide
  5. extractionafter which the aqueous alkaline phase was extracted with four 10-ml
  6. dry with materialThe combined benzene extracts were dried over fused potassium sulfate
  7. custom1-amino-3,5-di-n-butyl-adamantane hydrochloride was precipitated by exposure to dried hydrogen chloride gas

Sources & evidence

ORD record
ord-7de0d8aff9404887a63d6c32d87e37f6
Source dataset
uspto-grants-1978_10
Patent number
US04122193

Reaction notes

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